U.S. patent application number 15/187665 was filed with the patent office on 2017-06-22 for organic light-emitting device.
The applicant listed for this patent is SAMSUNG DISPLAY CO., LTD.. Invention is credited to Naoyuki Ito, Hyein Jeong, Seulong Kim, Younsun Kim, Jungsub Lee, Jino Lim, Dongwoo Shin.
Application Number | 20170179396 15/187665 |
Document ID | / |
Family ID | 57153266 |
Filed Date | 2017-06-22 |
United States Patent
Application |
20170179396 |
Kind Code |
A1 |
Kim; Seulong ; et
al. |
June 22, 2017 |
ORGANIC LIGHT-EMITTING DEVICE
Abstract
An organic light-emitting device including: a first electrode; a
second electrode facing the first electrode; an emission layer
between the first electrode and the second electrode; a hole
transport region between the first electrode and the emission
layer; and an electron transport region between the emission layer
and the second electrode, wherein the emission layer includes a
first compound represented by one of selected from Formulae 1A to
1E, and at least one selected from the hole transport region and
the electron transport region includes a second compound
represented by Formula 2A or 2B: ##STR00001##
Inventors: |
Kim; Seulong; (Yongin-si,
KR) ; Kim; Younsun; (Yongin-si, KR) ; Shin;
Dongwoo; (Yongin-si, KR) ; Lee; Jungsub;
(Yongin-si, KR) ; Ito; Naoyuki; (Yongin-si,
KR) ; Lim; Jino; (Yongin-si, KR) ; Jeong;
Hyein; (Yongin-si, KR) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
SAMSUNG DISPLAY CO., LTD. |
Yongin-si |
|
KR |
|
|
Family ID: |
57153266 |
Appl. No.: |
15/187665 |
Filed: |
June 20, 2016 |
Current U.S.
Class: |
1/1 |
Current CPC
Class: |
H01L 51/5012 20130101;
H01L 51/0072 20130101; C09K 11/025 20130101; H01L 51/5072 20130101;
H01L 51/0073 20130101; H01L 51/5004 20130101; H01L 51/0067
20130101; H01L 51/504 20130101; H01L 2251/5384 20130101; H01L
51/5262 20130101; H01L 51/0054 20130101; H01L 51/0071 20130101;
H01L 2251/552 20130101; H01L 51/0074 20130101; H01L 51/506
20130101; H01L 51/0058 20130101; H01L 51/0052 20130101; H01L
51/5016 20130101; H01L 51/5056 20130101 |
International
Class: |
H01L 51/00 20060101
H01L051/00; C09K 11/02 20060101 C09K011/02; H01L 51/50 20060101
H01L051/50 |
Foreign Application Data
Date |
Code |
Application Number |
Dec 22, 2015 |
KR |
10-2015-0184075 |
Claims
1. An organic light-emitting device comprising: a first electrode;
a second electrode facing the first electrode; an emission layer
between the first electrode and the second electrode; a hole
transport region between the first electrode and the emission
layer; and an electron transport region between the emission layer
and the second electrode, wherein the emission layer comprises a
first compound, at least one selected from the hole transport
region and the electron transport region comprises a second
compound, the first compound is represented by one selected from
Formulae 1A to 1E, and the second compound is represented by
Formula 2A or 2B: ##STR00237## ##STR00238## wherein, in Formulae 1A
to 1E, 2A, and 2B, rings A.sub.11 to A.sub.13 are each
independently selected from a C.sub.6-C.sub.60 aromatic group, a
C.sub.1-C.sub.60 heteroaromatic group, and a C.sub.6-C.sub.60
non-aromatic condensed polycyclic group, rings A.sub.21, A.sub.22,
and A.sub.23 are each independently selected from a
C.sub.5-C.sub.60 carbocyclic group and a C.sub.1-C.sub.80
heterocyclic group, each substituted with at least one
*-[(L.sub.22).sub.a22-(R.sub.22).sub.b22], each T.sub.11 and each
T.sub.12 are independently selected from carbon and nitrogen, two
or more of the three T.sub.11(s) in Formula 2A are identical to or
different from each other, T.sub.13 is N or C(R.sub.27), T.sub.14
is N or C(R.sub.28), two or more of the three T.sub.12(s) in
Formula 2A are identical to or different from each other, the two
T.sub.11(s) in Formula 2B are identical to or different from each
other, the two T.sub.12(s) in Formula 2B are identical to or
different from each other, and each bond between T.sub.11 and
T.sub.12 is a single bond or a double bond; wherein the three
T.sub.11(s) and the three T.sub.12(s) in Formula 2A are not all
nitrogen, and the two T.sub.11(s), the two T.sub.12(s), and
T.sub.13 and T.sub.14 in Formula 2B are not all nitrogen, rings
A.sub.21, A.sub.22, and A.sub.23 are each fused with a central
7-membered ring in Formulae 2A and 2B, such that they each share a
T.sub.11 and a T.sub.12 with the central 7-membered ring, X.sub.11
is N or C[(L.sub.3).sub.a3-(R.sub.3).sub.b3], and X.sub.12 is N or
C[(L.sub.4).sub.a4-(R.sub.4).sub.b4], X.sub.21 is selected from O,
S, Se, C(R.sub.23)(R.sub.24), Si(R.sub.23)(R.sub.24), and
N[(L.sub.21).sub.a21-(R.sub.21).sub.b21], L.sub.1 to L.sub.9 are
each independently selected from a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkylene group, a substituted or
unsubstituted C.sub.1-C.sub.10 heterocycloalkylene group, a
substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenylene
group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkenylene group, a substituted or unsubstituted
C.sub.6-C.sub.60 arylene group, a substituted or unsubstituted
C.sub.1-C.sub.60 heteroarylene group, and a substituted or
unsubstituted divalent non-aromatic condensed polycyclic group,
L.sub.21 and L.sub.22 are each independently selected from a
substituted or unsubstituted C.sub.3-C.sub.18 cycloalkylene group,
a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkylene
group, a substituted or unsubstituted C.sub.3-C.sub.10
cycloalkenylene group, a substituted or unsubstituted
C.sub.1-C.sub.10 heterocycloalkenylene group, a substituted or
unsubstituted C.sub.6-C.sub.60 arylene group, a substituted or
unsubstituted C.sub.1-C.sub.60 heteroarylene group, a substituted
or unsubstituted divalent non-aromatic condensed polycyclic group,
and a substituted or unsubstituted divalent non-aromatic condensed
heteropolycyclic group, a1 to a9, a21, and a22 are each
independently an integer selected from 0 to 5, R.sub.1 to R.sub.9
are each independently selected from hydrogen, deuterium, --F,
--Cl, --Br, --I, a hydroxyl group, a cyano group, a nitro group, an
amidino group, a hydrazino group, a hydrazono group, a substituted
or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or
unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or
unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or
unsubstituted C.sub.1-C.sub.60 alkoxy group, a substituted or
unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or
unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a
substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a
substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl
group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group,
a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a
substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a
substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a
substituted or unsubstituted monovalent non-aromatic condensed
polycyclic group, --Si(Q.sub.1)(Q.sub.2)(Q.sub.3),
--N(Q.sub.1)(Q.sub.2), --B(Q.sub.1)(Q.sub.2), --C(.dbd.O)(Q.sub.1),
--S(.dbd.O).sub.2(Q.sub.1), and --P(.dbd.O)(Q.sub.1)(Q.sub.2),
R.sub.21 to R.sub.24, R.sub.27, and R.sub.28 are each independently
selected from hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl
group, a cyano group, a nitro group, an amidino group, a hydrazino
group, a hydrazono group, a substituted or unsubstituted
C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted
C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted
C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted
C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted
C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or
unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or
unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl group, a
substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a
substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a
substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a
substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a
substituted or unsubstituted monovalent non-aromatic condensed
polycyclic group, a substituted or unsubstituted monovalent
non-aromatic condensed heteropolycyclic group,
--Si(Q.sub.4)(Q.sub.5)(Q.sub.6), --N(Q.sub.4)(Q.sub.5),
--B(Q.sub.4)(Q.sub.5), --C(.dbd.O)(Q.sub.4),
--S(.dbd.O).sub.2(Q.sub.4), and --P(.dbd.O)(Q.sub.4)(Q.sub.5), b1
to b9, b21, and b22 are each independently an integer selected from
1 to 3, c1, c2, and c5 to c7 are each independently an integer
selected from 0 to 10, provided that the sum of c5, c6, and c7 is 1
or more, c8 and c9 are each independently an integer selected from
0 to 4, provided that the sum of c8 and c9 is 1 or more, and at
least one substituent of the substituted C.sub.3-C.sub.10
cycloalkylene group, substituted C.sub.1-C.sub.10
heterocycloalkylene group, substituted C.sub.3-C.sub.10
cycloalkenylene group, substituted C.sub.1-C.sub.10
heterocycloalkenylene group, substituted C.sub.6-C.sub.60 arylene
group, substituted C.sub.1-C.sub.60 heteroarylene group, a
substituted divalent non-aromatic condensed polycyclic group,
substituted divalent non-aromatic condensed heteropolycyclic group,
substituted C.sub.1-C.sub.60 alkyl group, substituted
C.sub.2-C.sub.60 alkenyl group, substituted C.sub.2-C.sub.60
alkynyl group, substituted C.sub.1-C.sub.60 alkoxy group,
substituted C.sub.3-C.sub.10 cycloalkyl group, substituted
C.sub.1-C.sub.10 heterocycloalkyl group, substituted
C.sub.3-C.sub.10 cycloalkenyl group, substituted C.sub.1-C.sub.10
heterocycloalkenyl group, substituted C.sub.6-C.sub.60 aryl group,
substituted C.sub.6-C.sub.60 aryloxy group, substituted
C.sub.6-C.sub.60 arylthio group, substituted C.sub.1-C.sub.60
heteroaryl group, substituted monovalent non-aromatic condensed
polycyclic group, and substituted monovalent non-aromatic condensed
heteropolycyclic group is selected from the group consisting of:
deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a cyano group, a
nitro group, an amidino group, a hydrazino group, a hydrazono
group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl
group, a C.sub.2-C.sub.60 alkynyl group, and a C.sub.1-C.sub.60
alkoxy group; a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60
alkenyl group, a C.sub.2-C.sub.60 alkynyl group, and a
C.sub.1-C.sub.60 alkoxy group, each substituted with at least one
selected from deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.3-C.sub.10 cycloalkyl group, a
C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10
cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a
C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a
C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl
group, a monovalent non-aromatic condensed polycyclic group, a
monovalent non-aromatic condensed heteropolycyclic group,
--Si(Q.sub.11)(Q.sub.12)(Q.sub.13), --N(Q.sub.11)(Q.sub.12),
--B(Q.sub.11)(Q.sub.12), --C(.dbd.O)(Q.sub.11),
--S(.dbd.O).sub.2(Q.sub.11), and --P(.dbd.O)(Q.sub.11)(Q.sub.12), a
C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60
arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, a monovalent non-aromatic
condensed heteropolycyclic group, a biphenyl group, and a terphenyl
group; a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60
arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, and a monovalent
non-aromatic condensed heteropolycyclic group, each substituted
with at least one selected from deuterium, --F, --Cl, --Br, --I, a
hydroxyl group, a cyano group, a nitro group, an amidino group, a
hydrazino group, a hydrazono group, a C.sub.1-C.sub.60 alkyl group,
a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group,
a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl
group, a C.sub.1-C.sub.10 heterocycloalkyl group, a
C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10
heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a
C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group,
a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic
condensed polycyclic group, a monovalent non-aromatic condensed
heteropolycyclic group, --Si(Q.sub.21)(Q.sub.22)(Q.sub.23),
--N(Q.sub.21)(Q.sub.22), --B(Q.sub.21)(Q.sub.22),
--C(.dbd.O)(Q.sub.21), --S(.dbd.O).sub.2(Q.sub.21), and
--P(.dbd.O)(Q.sub.21)(Q.sub.22); and
--Si(Q.sub.31)(Q.sub.32)(Q.sub.33), --N(Q.sub.31)(Q.sub.32),
--B(Q.sub.31)(Q.sub.32), --C(.dbd.O)(Q.sub.31),
--S(.dbd.O).sub.2(Q.sub.31), and --P(.dbd.O)(Q.sub.31)(Q.sub.32),
wherein Q.sub.1 to Q.sub.6, Q.sub.11 to Q.sub.13, Q.sub.21 to
Q.sub.23, and Q.sub.31 to Q.sub.33 are each independently selected
from hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60
alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60
alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a
C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10
cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a
C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryl group
substituted with a C.sub.1-C.sub.60 alkyl group, a C.sub.6-C.sub.60
aryl group substituted with a C.sub.6-C.sub.60 aryl group, a
terphenyl group, a C.sub.1-C.sub.60 heteroaryl group, a
C.sub.1-C.sub.60 heteroaryl group substituted with a
C.sub.1-C.sub.60 alkyl group, a C.sub.1-C.sub.60 heteroaryl group
substituted with a C.sub.6-C.sub.60 aryl group, a monovalent
non-aromatic condensed polycyclic group, and a monovalent
non-aromatic condensed heteropolycyclic group.
2. The organic light-emitting device of claim 1, wherein: rings
A.sub.11 to A.sub.13 in Formulae 1A to 1D are each independently
selected from a benzene group, a naphthalene group, an anthracene
group, a phenanthrene group, a pyrene group, a triphenylene group,
an indene group, a fluorene group, a benzofluorene group, a
spiro-bifluorene group, a pyridine group, a pyrazine group, a
pyrimidine group, a pyridazine group, a pyrrole group, an imidazole
group, a quinoline group, an isoquinoline group, a quinoxaline
group, a quinazoline group, a triazine group, an indenopyrazine
group, an indenopyridine group, a phenanthroline group, and a
phenanthridine group.
3. The organic light-emitting device of claim 1, wherein: rings
A.sub.21, A.sub.22, and A.sub.23 in Formulae 2A and 2B are each
independently selected from a benzene group, a naphthalene group,
an anthracene group, an indene group, a fluorene group, a pyridine
group, a pyrimidine group, a pyrazine group, a pyridazine group, a
quinoline group, an isoquinoline group, a pyrrole group, a pyrazole
group, an imidazole group, an oxazole group, a thiazole group, a
cyclopentadiene group, a silole group, a selenophene group, a furan
group, a thiophene group, an indole group, a benzimidazole group, a
benzoxazole group, a benzothiazole group, an indene group, a
benzosilole group, a benzoselenophene group, a benzofuran group, a
benzothiophene group, a carbazole group, a fluorene group, a
dibenzosilole group, a dibenzoselenophene group, a dibenzofuran
group, a dibenzothiophene group, a pyrrolopyridine group, a
cyclopentapyridine group, a silolopyridine group, a
selenophenopyridine group, a furopyridine group, a thienopyridine
group, a pyrrolopyrimidine group, a cyclopentapyrimidine group, a
silolopyrimidine group, a selenophenopyrimidine group, a
furopyrimidine group, a thienopyrimidine group, a pyrrolopyrazine
group, a cyclopentapyrazine group, a silolopyrazine group, a
selenophenopyrazine group, a furopyrazine group, a thienopyrazine
group, a naphthopyrrole group, a cyclopentanaphthalene group, a
naphthosilole group, a naphthoselenothiophene group, a naphthofuran
group, a naphthothiophene group, a pyrroloquinoline group, a
cyclopentaquinoline group, a siloloquinoline group, a
selenophenoquinoline group, a furoquinoline group, a
thienoquinoline group, a pyrroloisoquinoline group, a
cyclopentaisoquinoline group, a siloloisoquinoline group, a
selenophenoisoquinoline group, a furoisoquinoline group, a
thienoisoquinoline group, an azacarbazole group, an azafluorene
group, an azadibenzosilole group, an azadibenzoselenophene group,
an azadibenzofuran group, an azadibenzothiophene group, an
indenoquinoline group, an indenoisoquinoline group, an
indenoquinoxaline group, a phenanthroline group, and an
naphthoindole group, each substituted with at least one
*-[(L.sub.22).sub.a22-(R.sub.22).sub.b22].
4. The organic light-emitting device of claim 1, wherein: rings
A.sub.21 A.sub.22, and A.sub.23 in Formulae 2A and 2B are each
independently selected from groups represented by Formulae 2-1 to
2-36, each substituted with at least one
*-[(L.sub.22).sub.a22-(R.sub.22).sub.b22)]: ##STR00239##
##STR00240## ##STR00241## ##STR00242## ##STR00243## wherein, in
Formulae 2-1 to 2-36, T.sub.11 and T.sub.12 are each independently
the same as described herein in connection with Formulae 2A and 2B,
X.sub.22 and X.sub.23 are each independently selected from O, S,
Se, a moiety comprising C, a moiety comprising N, and a moiety
comprising Si, and T.sub.21 to T.sub.28 are each independently
selected from N and a moiety comprising C.
5. The organic light-emitting device of claim 1, wherein X.sub.21
in Formulae 2A and 2B is
N[(L.sub.21).sub.a21-(R.sub.21).sub.b21].
6. The organic light-emitting device of claim 4, wherein: X.sub.21
in Formulae 2A and 2B is O, S, Se, C(R.sub.23)(R.sub.24), or
Si(R.sub.23)(R.sub.24), at least one selected from rings A.sub.21,
A.sub.22 and A.sub.23 in Formula 2A and at least one selected from
rings A.sub.21 and A.sub.23 in Formula 2B are each independently
selected from groups represented by Formulae 2-1 to 2-3, 2-10 to
2-27, and 2-33 to 2-36, and X.sub.22 or X.sub.23 in Formulae 2-1 to
2-3, 2-10 to 2-27, and 2-33 to 2-36 is
N-[(L.sub.22).sub.a22-(R.sub.22).sub.b22].
7. The organic light-emitting device of claim 1, wherein: in
Formulae 1A to 1E, 2A, and 2B, L.sub.1 to L.sub.9 and L.sub.21 and
L.sub.22 are each independently selected from the group consisting
of: a phenylene group, a pentalenylene group, an indenylene group,
a naphthylene group, an azulenylene group, an indacenylene group,
an acenaphthylene group, a fluorenylene group, a
spiro-bifluorenylene group, a spiro-benzofluorene-fluorenylene
group, a benzofluorenylene group, a dibenzofluorenylene group, a
phenalenylene group, a phenanthrenylene group, an anthracenylene
group, a fluoranthenylene group, a triphenylenylene group, a
pyrenylene group, a chrysenylene group, a perylenylene group, a
pentaphenylene group, a pyrrolylene group, a thiophenylene group, a
furanylene group, a silolylene group, an imidazolylene group, a
pyrazolylene group, a thiazolylene group, an isothiazolylene group,
an oxazolylene group, an isoxazolylene group, a pyridinylene group,
a pyrazinylene group, a pyrimidinylene group, a pyridazinylene
group, an indolylene group, an isoindolylene group, an indazolylene
group, a purinylene group, a quinolinylene group, an
isoquinolinylene group, a benzoquinolinylene group, a
phthalazinylene group, a naphthyridinylene group, a quinoxalinylene
group, a quinazolinylene group, a cinnolinylene group, a
phenanthridinylene group, an acridinylene group, a
phenanthrolinylene group, a phenazinylene group, a
benzimidazolylene group, a benzofuranylene group, a
benzothiophenylene group, a benzosilolylene group, an
isobenzothiazolylene group, a benzoxazolylene group, an
isobenzoxazolylene group, a triazolylene group, a tetrazolylene
group, an oxadiazolylene group, a triazinylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
dibenzosilolylene group, a carbazolylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, a
thiadiazolylene group, an imidazopyridinylene group, an
imidazopyrimidinylene group, an oxazolopyridinylene group, a
thiazolopyridinylene group, a benzonaphthyridinylene group, an
azafluorenylene group, an azaspiro-bifluorenylene group, an
azacarbazolylene group, an azadibenzofuranylene group, an
azadibenzothiophenylene group, and an azadibenzosilolylene group;
and a phenylene group, a pentalenylene group, an indenylene group,
a naphthylene group, an azulenylene group, an indacenylene group,
an acenaphthylene group, a fluorenylene group, a
spiro-bifluorenylene group, a spiro-benzofluorene-fluorenylene
group, a benzofluorenylene group, a dibenzofluorenylene group, a
phenalenylene group, a phenanthrenylene group, an anthracenylene
group, a fluoranthenylene group, a triphenylenylene group, a
pyrenylene group, a chrysenylene group, a perylenylene group, a
pentaphenylene group, a pyrrolylene group, a thiophenylene group, a
furanylene group, a silolylene group, an imidazolylene group, a
pyrazolylene group, a thiazolylene group, an isothiazolylene group,
an oxazolylene group, an isoxazolylene group, a pyridinylene group,
a pyrazinylene group, a pyrimidinylene group, a pyridazinylene
group, an indolylene group, an isoindolylene group, an indazolylene
group, a purinylene group, a quinolinylene group, an
isoquinolinylene group, a benzoquinolinylene group, a
phthalazinylene group, a naphthyridinylene group, a quinoxalinylene
group, a quinazolinylene group, a cinnolinylene group, a
phenanthridinylene group, an acridinylene group, a
phenanthrolinylene group, a phenazinylene group, a
benzimidazolylene group, a benzofuranylene group, a
benzothiophenylene group, a benzosilolylene group, an
isobenzothiazolylene group, a benzoxazolylene group, an
isobenzoxazolylene group, a triazolylene group, a tetrazolylene
group, an oxadiazolylene group, a triazinylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
dibenzosilolylene group, a carbazolylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, a
thiadiazolylene group, an imidazopyridinylene group, an
imidazopyrimidinylene group, an oxazolopyridinylene group, a
thiazolopyridinylene group, a benzonaphthyridinylene group, an
azafluorenylene group, an azaspiro-bifluorenylene group, an
azacarbazolylene group, an azadibenzofuranylene group, an
azadibenzothiophenylene group, and an azadibenzosilolylene group,
each substituted with at least one selected from deuterium, --F,
--Cl, --Br, --I, a hydroxyl group, a cyano group, a nitro group, an
amidino group, a hydrazino group, a hydrazono group, a
C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a
C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, a monovalent non-aromatic
condensed heteropolycyclic group, a biphenyl group, a terphenyl
group, --Si(Q.sub.31)(Q.sub.32)(Q.sub.33), --N(Q.sub.31)(Q.sub.32),
--B(Q.sub.31)(Q.sub.32), --C(.dbd.O)(Q.sub.31),
--S(.dbd.O).sub.2(Q.sub.31), and --P(.dbd.O)(Q.sub.31)(Q.sub.32);
and L.sub.1 to L.sub.9 are each not a substituted or unsubstituted
carbazolylene group, a substituted or unsubstituted
dibenzofuranylene group, a substituted or unsubstituted
dibenzothiophenylene group, a substituted or unsubstituted
dibenzosilolylene group, or a substituted or unsubstituted
dibenzocarbazolylene group, wherein Q.sub.31 to Q.sub.33 are each
independently selected from the group consisting of: a
C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a
phenyl group, a biphenyl group, a terphenyl group, a naphthyl
group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a
quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, and
a quinazolinyl group; and a phenyl group, a biphenyl group, a
terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl
group, a pyrazinyl group, a quinolinyl group, an isoquinolinyl
group, a quinoxalinyl group, and a quinazolinyl group, each
substituted with at least one selected from a C.sub.1-C.sub.10
alkyl group, a C.sub.1-C.sub.10 alkoxy group, and a phenyl
group.
8. The organic light-emitting device of claim 1, wherein: in
Formulae 1A to 1E, 2A, and 2B, L.sub.1 to L.sub.9, L.sub.21, and
L.sub.22 are each independently selected from the group consisting
of: a phenylene group, a pentalenylene group, an indenylene group,
a naphthylene group, an azulenylene group, an indacenylene group,
an acenaphthylene group, a fluorenylene group, a
spiro-bifluorenylene group, a benzofluorenylene group, a
dibenzofluorenylene group, a phenalenylene group, a
phenanthrenylene group, an anthracenylene group, a fluoranthenylene
group, a triphenylenylene group, a pyrenylene group, a chrysenylene
group, a perylenylene group, a pentaphenylene group, a hexacenylene
group, a pyrrolylene group, a thiophenylene group, a furanylene
group, a silolylene group, an indolylene group, an isoindolylene
group, a benzofuranylene group, a benzothiophenylene group, a
benzosilolylene group, a dibenzofuranylene group, a
dibenzothiophenylene group, a dibenzosilolylene group, a
carbazolylene group, a benzocarbazolylene group, a
dibenzocarbazolylene group, and a pyridinylene group; and a
phenylene group, a pentalenylene group, an indenylene group, a
naphthylene group, an azulenylene group, an indacenylene group, an
acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene
group, a benzofluorenylene group, a dibenzofluorenylene group, a
phenalenylene group, a phenanthrenylene group, an anthracenylene
group, a fluoranthenylene group, a triphenylenylene group, a
pyrenylene group, a chrysenylene group, a perylenylene group, a
pentaphenylene group, a hexacenylene group, a pyrrolylene group, a
thiophenylene group, a furanylene group, a silolylene group, an
indolylene group, an isoindolylene group, a benzofuranylene group,
a benzothiophenylene group, a benzosilolylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
dibenzosilolylene group, a carbazolylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, and a
pyridinylene group, each substituted with at least one selected
from deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a cyano
group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl
group, an indacenyl group, an acenaphthyl group, a fluorenyl group,
a spiro-bifluorenylene group, a benzofluorenyl group, a
dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group,
an anthracenyl group, a fluoranthenyl group, a triphenylenyl group,
a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pyrrolyl group, a
thiophenyl group, a furanyl group, a silolyl group, a an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a benzosilolyl group, a dibenzofuranyl group, a
dibenzothiophenyl group, a dibenzosilolyl group, a carbazolyl
group, a benzocarbazolyl group, a dibenzocarbazolyl group, a
pyridinyl group, --Si(Q.sub.31)(Q.sub.32)(Q.sub.33)
--N(Q.sub.31)(Q.sub.32), --B(Q.sub.31)(Q.sub.32),
--C(.dbd.O)(Q.sub.31), --S(.dbd.O).sub.2(Q.sub.31), and
--P(.dbd.O)(Q.sub.31)(Q.sub.32), L.sub.1 to L.sub.9 are each not a
substituted or unsubstituted carbazolylene group, a substituted or
unsubstituted dibenzofuranylene group, a substituted or
unsubstituted dibenzothiophenylene group, a substituted or
unsubstituted dibenzosilolylene group, or a substituted or
unsubstituted dibenzocarbazolylene group, Q31 to Q.sub.33 are each
independently selected from the group consisting of: a
C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a
phenyl group, a biphenyl group, a terphenyl group, a naphthyl
group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a
quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, and
a quinazolinyl group; and a phenyl group, a biphenyl group, a
terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl
group, a pyrazinyl group, a quinolinyl group, an isoquinolinyl
group, a quinoxalinyl group, and a quinazolinyl group, each
substituted with at least one selected from a C.sub.1-C.sub.10
alkyl group, a C.sub.1-C.sub.10 alkoxy group, and a phenyl
group.
9. The organic light-emitting device of claim 1, wherein: in
Formulae 1A to 1E, 2A, and 2B, R.sub.1 to R.sub.9 are each
independently selected from the group consisting of: hydrogen,
deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a cyano group, a
nitro group, an amidino group, a hydrazino group, a hydrazono
group, a C.sub.1-C.sub.20 alkyl group, and a C.sub.1-C.sub.20
alkoxy group; a cyclopentyl group, a cyclohexyl group, a
cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a
phenyl group, a biphenyl group, a terphenyl group, a pentalenyl
group, an indenyl group, a naphthyl group, an azulenyl group, an
indacenyl group, an acenaphthyl group, a fluorenyl group, a
spiro-bifluorenyl group, a spiro-benzofluorene-fluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group,
a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group,
a triphenylenyl group, a pyrenyl group, a chrysenyl group, a
perylenyl group, a pentaphenyl group, a pyrrolyl group, a
thiophenyl group, a furanyl group, a silolyl group, an imidazolyl
group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group,
an oxazolyl group, an isoxazolyl group, a pyridinyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an
indolyl group, an isoindolyl group, an indazolyl group, a purinyl
group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl
group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl
group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group,
a benzofuranyl group, a benzothiophenyl group, a benzosilyl group,
an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
oxadiazolyl group, a triazinyl group, a benzocarbazolyl group, a
thiadiazolyl group, an imidazopyridinyl group, an
imidazopyrimidinyl group, an oxazolopyridinyl group, a
thiazolopyridinyl group, a benzonaphthyridinyl group, an
azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl
group, an azadibenzofuranyl group, an azadibenzothiophenyl group,
an azadibenzosilolyl group, --Si(Q.sub.1)(Q.sub.2)(Q.sub.3),
--N(Q.sub.1)(Q.sub.2), --B(Q.sub.1(Q.sub.2), --C(.dbd.O)(Q.sub.1),
--S(.dbd.O).sub.2(Q.sub.1), and --P(.dbd.O)(Q.sub.1)(Q.sub.2); and
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a
cyclopentenyl group, a cyclohexenyl group, a phenyl group, a
biphenyl group, a terphenyl group, a pentalenyl group, an indenyl
group, a naphthyl group, an azulenyl group, an indacenyl group, an
acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a
spiro-benzofluorene-fluorenyl group, a benzofluorenyl group, a
dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group,
an anthracenyl group, a fluoranthenyl group, a triphenylenyl group,
a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a pyrrolyl group, a thiophenyl group, a furanyl
group, a silolyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, an isothiazolyl group, an oxazolyl group, an
isoxazolyl group, a pyridinyl group, a pyrazinyl group, a
pyrimidinyl group, a pyridazinyl group, an indolyl group, an
isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl
group, an isoquinolinyl group, a benzoquinolinyl group, a
phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a
quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an
acridinyl group, a phenanthrolinyl group, a phenazinyl group, a
benzimidazolyl group, a benzofuranyl group, a benzothiophenyl
group, a benzosilolyl group, an isobenzothiazolyl group, a
benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a
tetrazolyl group, an oxadiazolyl group, a triazinyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl
group, an imidazopyridinyl group, an imidazopyrimidinyl group, an
oxazolopyridinyl group, a thiazolopyridinyl group, a
benzonaphthyridinyl group, an azafluorenyl group, an
azaspiro-bifluorenyl group, an azacarbazolyl group, an
azadibenzofuranyl group, an azadibenzothiophenyl group, and an
azadibenzosilolyl group, each substituted with at least one
selected from deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a
C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10
cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a
C.sub.6-C.sub.60 aryl group, a C.sub.1-C.sub.60 heteroaryl group, a
monovalent non-aromatic condensed polycyclic group, a monovalent
non-aromatic condensed heteropolycyclic group, a biphenyl group, a
terphenyl group, --Si(Q.sub.31)(Q.sub.32)(Q.sub.33),
--N(Q.sub.31)(Q.sub.32), --B(Q.sub.31)(Q.sub.32),
--C(.dbd.O)(Q.sub.31), --S(.dbd.O).sub.2(Q.sub.31), and
--P(.dbd.O)(Q.sub.31)(Q.sub.32), R.sub.21 to R.sub.24, R.sub.27,
and R.sub.28 are each independently selected from the group
consisting of: hydrogen, deuterium, --F, --Cl, --Br, --I, a
hydroxyl group, a cyano group, a nitro group, an amidino group, a
hydrazino group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group,
and a C.sub.1-C.sub.20 alkoxy group; a cyclopentyl group, a
cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a
cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl
group, a pentalenyl group, an indenyl group, a naphthyl group, an
azulenyl group, an indacenyl group, an acenaphthyl group, a
fluorenyl group, a spiro-bifluorenyl group, a
spiro-benzofluorene-fluorenyl group, a benzofluorenyl group, a
dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group,
an anthracenyl group, a fluoranthenyl group, a triphenylenyl group,
a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a pyrrolyl group, a thiophenyl group, a furanyl
group, a silolyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, an isothiazolyl group, an oxazolyl group, an
isoxazolyl group, a pyridinyl group, a pyrazinyl group, a
pyrimidinyl group, a pyridazinyl group, an indolyl group, an
isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl
group, an isoquinolinyl group, a benzoquinolinyl group, a
phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a
quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an
acridinyl group, a phenanthrolinyl group, a phenazinyl group, a
benzimidazolyl group, a benzofuranyl group, a benzothiophenyl
group, a benzosilolyl group, an isobenzothiazolyl group, a
benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a
tetrazolyl group, an oxadiazolyl group, a triazinyl group, a
dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl
group, a carbazolyl group, a benzocarbazolyl group, a
dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl
group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a
thiazolopyridinyl group, a benzonaphthyridinyl group, an
azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl
group, an azadibenzofuranyl group, an azadibenzothiophenyl group,
an azadibenzosilolyl group, --Si(Q.sub.4)(Q.sub.5)(Q.sub.6),
--N(Q.sub.4)(Q.sub.5), --B(Q.sub.4)(Q.sub.5), --C(.dbd.O)(Q.sub.4),
--S(.dbd.O).sub.2(Q.sub.4), and --P(.dbd.O)(Q.sub.4)(Q.sub.5); and
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a
cyclopentenyl group, a cyclohexenyl group, a phenyl group, a
biphenyl group, a terphenyl group, a pentalenyl group, an indenyl
group, a naphthyl group, an azulenyl group, an indacenyl group, an
acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a
spiro-benzofluorene-fluorenyl group, a benzofluorenyl group, a
dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group,
an anthracenyl group, a fluoranthenyl group, a triphenylenyl group,
a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl
group, a perylenyl group, a pentaphenyl group, a pyrrolyl group, a
thiophenyl group, a furanyl group, a silolyl group, an imidazolyl
group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group,
an oxazolyl group, an isoxazolyl group, a pyridinyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an
indolyl group, an isoindolyl group, an indazolyl group, a purinyl
group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl
group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl
group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group,
a benzofuranyl group, a benzothiophenyl group, a benzosilolyl
group, an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a
dibenzothiophenyl group, a dibenzosilolyl group, a carbazolyl
group, a benzocarbazolyl group, a dibenzocarbazolyl group, a
thiadiazolyl group, an imidazopyridinyl group, an
imidazopyrimidinyl group, an oxazolopyridinyl group, a
thiazolopyridinyl group, a benzonaphthyridinyl group, an
azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl
group, an azadibenzofuranyl group, an azadibenzothiophenyl group,
and an azadibenzosilolyl group, each substituted with at least one
selected from deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a
C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10
cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a
C.sub.6-C.sub.60 aryl group, a C.sub.1-C.sub.60 heteroaryl group, a
monovalent non-aromatic condensed polycyclic group, a monovalent
non-aromatic condensed heteropolycyclic group, a biphenyl group, a
terphenyl group, --Si(Q.sub.31)(Q.sub.32)(Q.sub.33),
--N(Q.sub.31)(Q.sub.32), --B(Q.sub.31)(Q.sub.32),
--C(.dbd.O)(Q.sub.31), --S(.dbd.O).sub.2(Q.sub.31), and
--P(.dbd.O)(Q.sub.31)(Q.sub.32), wherein Q.sub.1 to Q.sub.6 and
Q.sub.31 to Q.sub.33 are each independently selected from the group
consisting of: a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
a naphthyl group, a pyridinyl group, a pyrimidinyl group, a
pyrazinyl group, a quinolinyl group, an isoquinolinyl group, a
quinoxalinyl group, and a quinazolinyl group; and a phenyl group, a
biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl
group, a pyrimidinyl group, a pyrazinyl group, a quinolinyl group,
an isoquinolinyl group, a quinoxalinyl group, and a quinazolinyl
group, each substituted with at least one selected from a
C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, and
a phenyl group.
10. The organic light-emitting device of claim 1, wherein: in
Formulae 1A to 1E, 2A, and 2B, R.sub.1 to R.sub.9 are each
independently selected from the group consisting of: hydrogen,
deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a cyano group, a
nitro group, an amidino group, a hydrazino group, a hydrazono
group, a C.sub.1-C.sub.20 alkyl group, and a C.sub.1-C.sub.20
alkoxy group; a phenyl group, a biphenyl group, a terphenyl group,
a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl
group, an indacenyl group, an acenaphthyl group, a fluorenyl group,
a spiro-bifluorenyl group, a benzofluorenyl group, a
dibenzofluorenyl group, a spiro-benzofluorene-fluorenyl group, an
indenofluorenyl group, a phenalenyl group, a phenanthrenyl group,
an anthracenyl group, a fluoranthenyl group, a triphenylenyl group,
a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pyrrolyl group, a
thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl
group, a thiazolyl group, an isothiazolyl group, an oxazolyl group,
an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a
pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an
indolyl group, an indazolyl group, a purinyl group, a quinolinyl
group, an isoquinolinyl group, a benzoquinolinyl group, a
phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a
quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an
acridinyl group, a phenanthrolinyl group, a phenazinyl group, a
benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl
group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl
group, an oxadiazolyl group, a triazinyl group, a thiadiazolyl
group, an imidazopyridinyl group, an imidazopyrimidinyl group,
--Si(Q.sub.1)(Q.sub.2)(Q.sub.3), --N(Q.sub.1)(Q.sub.2),
--B(Q.sub.1)(Q.sub.2), --C(.dbd.O)(Q.sub.1),
--S(.dbd.O).sub.2(Q.sub.1), and --P(.dbd.O)(Q.sub.1)(Q.sub.2); and
a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl
group, an indenyl group, a napthyl group, an azulenyl group, an
indacenyl group, an acenaphthyl group, a fluorenyl group, a
spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl
group, a spiro-benzofluorene-fluorenyl group, an indenofluorenyl
group, a phenalenyl group, a phenanthrenyl group, an anthracenyl
group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl
group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a
hexacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl
group, an imidazolyl group, a pyrazolyl group, a thiazolyl group,
an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a
pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a
pyridazinyl group, an isoindolyl group, an indolyl group, an
indazolyl group, a purinyl group, a quinolinyl group, an
isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group,
a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group,
a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group,
an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
oxadiazolyl group, a triazinyl group, a thiadiazolyl group, an
imidazopyridinyl group, and an imidazopyrimidinyl group, each
substituted with at least one selected from deuterium, --F, --Cl,
--Br, --I, a hydroxyl group, a cyano group, a nitro group, an
amidino group, a hydrazino group, a hydrazono group, a
C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a
C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, a monovalent non-aromatic
condensed heteropolycyclic group, a biphenyl group, a terphenyl
group, --Si(Q.sub.31)(Q.sub.32)(Q.sub.33), --N(Q.sub.31)(Q.sub.32),
--B(Q.sub.31)(Q.sub.32), --C(.dbd.O)(Q.sub.31),
--S(.dbd.O).sub.2(Q.sub.31), and --P(.dbd.O)(Q.sub.31)(Q.sub.32),
R.sub.21 to R.sub.24, R.sub.27, and R.sub.28 are each independently
selected from the group consisting of: a phenyl group, a biphenyl
group, a terphenyl group, a pentalenyl group, an indenyl group, a
naphthyl group, an azulenyl group, an indacenyl group, an
acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a
spiro-benzofluorene-fluorenyl group, an indenofluorenyl group, a
phenalenyl group, a phenanthrenyl group, an anthracenyl group, a
fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a
chrysenyl group, a picenyl group, a perylenyl group, a pentaphenyl
group, a hexacenyl group, a pyrrolyl group, a thiophenyl group, a
furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl
group, an isothiazolyl group, an oxazolyl group, an isoxazolyl
group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a
pyridazinyl group, an isoindolyl group, an indolyl group, an
indazolyl group, a purinyl group, a quinolinyl group, an
isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group,
a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group,
a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an
acridinyl group, a phenanthrolinyl group, a phenazinyl group, a
benzimidazolyl group, a benzofuranyl group, a benzothiophenyl
group, an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a
dibenzothiophenyl group, a benzocarbazolyl group, a
dibenzocarbazolyl group, a dibenzosilolyl group, a thiadiazolyl
group, an imidazopyridinyl group, an imidazopyrimidinyl group,
--Si(Q.sub.4)(Q.sub.5)(Q.sub.6), --N(Q.sub.4)(Q.sub.5),
--B(Q.sub.4)(Q.sub.5), --C(.dbd.O)(Q.sub.4),
--S(.dbd.O).sub.2(Q.sub.4), and --P(.dbd.O)(Q.sub.4)(Q.sub.5); and
a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl
group, an indenyl group, a naphthyl group, an azulenyl group, an
indacenyl group, an acenaphthyl group, a fluorenyl group, a
spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl
group, a spiro-benzofluorene-fluorenyl group, an indenofluorenyl
group, a phenalenyl group, a phenanthrenyl group, an anthracenyl
group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl
group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a
pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl
group, an imidazolyl group, a pyrazolyl group, a thiazolyl group,
an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a
pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a
pyridazinyl group, an isoindolyl group, an indolyl group, an
indazolyl group, a purinyl group, a quinolinyl group, an
isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group,
a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group,
a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an
acridinyl group, a phenanthrolinyl group, a phenazinyl group, a
benzimidazolyl group, a benzofuranyl group, a benzothiophenyl
group, an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a
dibenzothiophenyl group, a benzocarbazolyl group, a
dibenzocarbazolyl group, a dibenzosilolyl group, a thiadiazolyl
group, an imidazopyridinyl group, and an imidazopyrimidinyl group,
each substituted with at least one selected from deuterium, --F,
--Cl, --Br, --I, a hydroxyl group, a cyano group, a nitro group, an
amidino group, a hydrazino group, a hydrazono group, a
C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a
C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, a monovalent non-aromatic
condensed heteropolycyclic group, a biphenyl group, a terphenyl
group, --Si(Q.sub.31)(Q.sub.32)(Q.sub.33), --N(Q.sub.31)(Q.sub.32),
--B(Q.sub.31)(Q.sub.32), --C(.dbd.O)(Q.sub.31),
--S(.dbd.O).sub.2(Q.sub.31), and --P(.dbd.O)(Q.sub.31)(Q.sub.32),
and R.sub.22 to R.sub.24, R.sub.27, and R.sub.28 are each
independently selected from hydrogen, deuterium, --F, --Cl, --Br,
--I, a hydroxyl group, a cyano group, a nitro group, an amidino
group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.20
alkyl group, a C.sub.1-C.sub.20 alkoxy group,
--Si(Q.sub.4)(Q.sub.5)(Q.sub.6), --S(.dbd.O).sub.2(Q.sub.4), and
--P(.dbd.O)(Q.sub.4)(Q.sub.5), wherein Q.sub.1 to Q.sub.6 and
Q.sub.31 to Q.sub.33 are each independently selected from the group
consisting of: a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
a naphthyl group, a pyridinyl group, a pyrimidinyl group, a
pyrazinyl group, a quinolinyl group, an isoquinolinyl group, a
quinoxalinyl group and a quinazolinyl group; and a phenyl group, a
biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl
group, a pyrimidinyl group, a pyrazinyl group, a quinolinyl group,
an isoquinolinyl group, a quinoxalinyl group, and a quinazolinyl
group, each substituted with at least one selected from a
C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, and
a phenyl group.
11. The organic light-emitting device of claim 1, wherein: the
first compound is represented by one selected from Formula 1E and
Formulae 1-1 to 1-6: ##STR00244## wherein Formula 1E is the same as
described above, rings A.sub.11 to A.sub.13, L.sub.1 to L.sub.6, a1
to a6, R.sub.1 to R.sub.6, and b1 to b6 in Formulae 1-1 to 1-6 are
each independently the same as described herein in connection with
Formulae 1A to 1D, c1, c2, and c6 are each independently an integer
selected from 0 to 10, and c5 is an integer selected from 1 to
10.
12. The organic light-emitting device of claim 1, wherein the
second compound has a triplet energy of 2.2 eV or more.
13. The organic light-emitting device of claim 1, wherein: the
emission layer comprises a first host and a second host, and the
first host comprises the first compound.
14. The organic light-emitting device of claim 1, wherein: the
electron transport region comprises a buffer layer, the buffer
layer directly contacts the emission layer, and the buffer layer
comprises the second compound.
15. The organic light-emitting device of claim 1, wherein the
emission layer comprises a dopant, wherein the dopant is an
organometallic complex.
16. The organic light-emitting device of claim 15, wherein the
organometallic complex is represented by Formula 401: ##STR00245##
wherein, in Formulae 401 and 402, M is selected from iridium (Ir),
platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti),
zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium
(Rh), and thulium (Tm), L.sub.401 is a ligand represented by
Formula 402, xc1 is 1, 2, or 3, and when xc1 is two or more, two or
more L.sub.401(s) are identical to or different from each other,
L.sub.402 is an organic ligand, xc2 is an integer selected from 0
to 4, and when xc2 is two or more, two or more L.sub.402(s) are
identical to or different from each other, X.sub.401 to X.sub.404
are each independently nitrogen or carbon, X.sub.401 is linked to
X.sub.403 via a single bond or a double bond, and X.sub.402 is
linked to X.sub.404 via a single bond or a double bond, A.sub.401
and A.sub.402 are each independently a C.sub.5-C.sub.60 carbocyclic
group or a C.sub.1-C.sub.60 heterocyclic group, X.sub.405 is a
single bond, *--O--*', *--S--*', *--C(.dbd.O)--*',
*--N(Q.sub.411)--*', *--C(Q.sub.411)(Q.sub.412)--*',
*--C(Q.sub.411)=C(Q.sub.412)-*', *--C(Q.sub.411)=*', or
*.dbd.C(Q.sub.411)=*', and Q.sub.411 and Q.sub.412 are each
independently hydrogen, deuterium, a C.sub.1-C.sub.20 alkyl group,
a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group,
a terphenyl group, or a naphthyl group, X.sub.406 is a single bond,
O, or S, and R.sub.401 and R.sub.402 are each independently
selected from hydrogen, deuterium, --F, --Cl, --Br, --I,
--CD.sub.3, --CF.sub.3, a hydroxyl group, a cyano group, a nitro
group, an amidino group, a hydrazino group, a hydrazono group, a
substituted or unsubstituted C.sub.1-C.sub.20 alkyl group, a
substituted or unsubstituted C.sub.1-C.sub.20 alkoxy group, a
substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a
substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl
group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl
group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkenyl group, a substituted or unsubstituted
C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted
C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted
C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted
C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted
monovalent non-aromatic condensed polycyclic group and a
substituted or unsubstituted monovalent non-aromatic condensed
heteropolycyclic group --Si(Q.sub.401)(Q.sub.402)(Q.sub.403),
--N(Q.sub.401)(Q.sub.402), --B(Q.sub.401)(Q.sub.402),
--C(.dbd.O)(Q.sub.401), --S(.dbd.O).sub.2(Q.sub.401), and
--P(.dbd.O)(Q.sub.401)(Q.sub.402), wherein Q.sub.401 to Q.sub.403
are each independently selected from a C.sub.1-C.sub.10 alkyl
group, a C.sub.1-C.sub.10 alkoxy group, a C.sub.6-C.sub.20 aryl
group, and a C.sub.1-C.sub.20 heteroaryl group, xc11 and xc12 are
each independently an integer selected from 0 to 10, and * and *'
in Formula 402 each independently indicate a binding site to M in
Formula 401.
17. The organic light-emitting device of claim 1, wherein: the
electron transport region comprises a buffer layer, an electron
transport layer, and an electron injection layer, and at least one
selected from the electron transport layer and the electron
injection layer comprises an alkali metal, an alkaline earth metal,
a rare earth metal, an alkali metal compound, an alkaline earth
metal compound, a rare earth metal compound, an alkali metal
complex, an alkaline earth metal complex, a rare earth metal
complex, or a combination thereof.
18. The organic light-emitting device of claim 1, wherein: the hole
transport region comprises a p-dopant, and the p-dopant has a
lowest unoccupied molecular orbital (LUMO) of -3.5 eV or less.
19. The organic light-emitting device of claim 18, wherein the
p-dopant comprises a cyano group-containing compound.
20. The organic light-emitting device of claim 1, wherein: the
emission layer comprises a first-color-light emitting-emission
layer, the organic light-emitting device further comprises i) at
least one second-color-light emitting-emission layer or ii) at
least one second-color-light emitting-emission layer and at least
one third-color-light emitting-emission layer, each between the
first electrode and the second electrode, a maximum emission
wavelength of the first-color-light emitting-emission layer, a
maximum emission wavelength of the second-color-light
emitting-emission layer, and a maximum emission wavelength of the
third-color-light emitting-emission layer are identical to or
different from each other, and the organic light-emitting device
emits a mixed light including a first-color-light and a
second-color-light, or a mixed light including the
first-color-light, the second-color-light, and a third-color-light.
Description
CROSS-REFERENCE TO RELATED APPLICATION
[0001] This application claims priority to and the benefit of
Korean Patent Application No. 10-2015-0184075, filed on Dec. 22,
2015 in the Korean Intellectual Property Office, the entire content
of which is incorporated herein by reference.
BACKGROUND
[0002] 1. Field
[0003] One or more aspects of example embodiments of the present
disclosure are related to an organic light-emitting device.
[0004] 2. Description of the Related Art
[0005] Organic light emitting devices are self-emission devices
that have wide viewing angles, high contrast ratios, short response
times, and/or excellent brightness, driving voltage, and/or
response speed characteristics compared to devices in the related
art.
[0006] An example organic light-emitting device may include a first
electrode on a substrate, and a hole transport region, an emission
layer, an electron transport region, and a second electrode
sequentially positioned on the first electrode. Holes provided from
the first electrode may move toward the emission layer through the
hole transport region, and electrons provided from the second
electrode may move toward the emission layer through the electron
transport region. Carriers (such as holes and electrons) may
recombine in the emission layer to produce excitons. These excitons
may transition (e.g., radiatively decay) from an excited state to a
ground state to thereby generate light.
SUMMARY
[0007] One or more aspects of example embodiments of the present
disclosure are directed toward an organic light-emitting device
having a low driving voltage and high efficiency.
[0008] Additional aspects will be set forth in part in the
description which follows and, in part, will be apparent from the
description, or may be learned by practice of the presented
embodiments.
[0009] One or more example embodiments of the present disclosure
provide an organic light-emitting device including:
[0010] a first electrode;
[0011] a second electrode facing the first electrode;
[0012] an emission layer between the first electrode and the second
electrode;
[0013] a hole transport region between the first electrode and the
emission layer; and
[0014] an electron transport region between the emission layer and
the second electrode, wherein:
[0015] the emission layer includes a first compound,
[0016] at least one selected from the hole transport region and the
electron transport region includes a second compound,
[0017] the first compound is represented by one selected from
Formulae 1A to 1E, and
[0018] the second compound is represented by Formula 2A or 2B:
##STR00002##
[0019] In Formulae 1A to 1E, 2A, and 2B,
[0020] rings A.sub.11 to A.sub.13 may each independently be
selected from a C.sub.6-C.sub.60 aromatic group, a C.sub.1-C.sub.60
heteroaromatic group, and a C.sub.6-C.sub.60 non-aromatic condensed
polycyclic group,
[0021] rings A.sub.21, A.sub.22, and A.sub.23 may each
independently be selected from a C.sub.5-C.sub.60 carbocyclic group
and a C.sub.1-C.sub.60 heterocyclic group, each substituted with at
least one *-[(L.sub.22).sub.a22-(R.sub.22).sub.b22],
[0022] each T.sub.11 and each T.sub.12 may independently be
selected from carbon (C) and nitrogen (N), two or more of the three
T.sub.11(s) in Formula 2A may be identical to or different from
each other, T.sub.13 may be N or C(R.sub.27), T.sub.14 may be N or
C(R.sub.28), two or more of the three T.sub.12(s) in Formula 2A may
be identical to or different from each other, the two T.sub.11(s)
in Formula 2B may be identical to or different from each other, the
two T.sub.12(s) in Formula 2B may be identical to or different from
each other, and each bond between T.sub.11 and T.sub.12 may be a
single bond or a double bond; wherein the three T.sub.11(s) and the
three T.sub.12(s) in Formula 2A are not all nitrogen, and the two
T.sub.11(s), the two T.sub.12(S), T.sub.13, and T.sub.14 in Formula
2B are not all nitrogen,
[0023] ring A.sub.21, A.sub.22, and A.sub.23 may each be condensed
(e.g., fused) with a central 7-membered ring in Formulae 2A and 2B,
such that they each share a T.sub.11 and a T.sub.12 with the
central 7-membered ring,
[0024] X.sub.11 may be N or C[(L.sub.3).sub.a3-(R.sub.3).sub.b3],
and X.sub.12 may be N or C[(L.sub.4).sub.a4-(R.sub.4).sub.b4],
[0025] X.sub.21 may be selected from oxygen (O), sulfur (S),
selenium (Se), C(R.sub.23)(R.sub.24), Si(R.sub.23)(R.sub.24), and
N[(L.sub.21).sub.a21-(R.sub.21).sub.b21],
[0026] L.sub.1 to L.sub.9 may each independently be selected from a
substituted or unsubstituted C.sub.3-C.sub.10 cycloalkylene group,
a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkylene
group, a substituted or unsubstituted C.sub.3-C.sub.10
cycloalkenylene group, a substituted or unsubstituted
C.sub.1-C.sub.10 heterocycloalkenylene group, a substituted or
unsubstituted C.sub.6-C.sub.60 arylene group, a substituted or
unsubstituted C.sub.1-C.sub.60 heteroarylene group, and a
substituted or unsubstituted divalent non-aromatic condensed
polycyclic group,
[0027] L.sub.21 and L.sub.22 may each independently be selected
from a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkylene
group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkylene group, a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkenylene group, a substituted or
unsubstituted C.sub.1-C.sub.10 heterocycloalkenylene group, a
substituted or unsubstituted C.sub.6-C.sub.60 arylene group, a
substituted or unsubstituted C.sub.1-C.sub.60 heteroarylene group,
a substituted or unsubstituted divalent non-aromatic condensed
polycyclic group, and a substituted or unsubstituted divalent
non-aromatic condensed heteropolycyclic group,
[0028] a1 to a9, a21, and a22 may each independently be an integer
selected from 0 to 5,
[0029] R.sub.1 to R.sub.9 may each independently be selected from
hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a substituted or unsubstituted C.sub.1-C.sub.60
alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60
alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60
alkynyl group, a substituted or unsubstituted C.sub.1-C.sub.60
alkoxy group, a substituted or unsubstituted C.sub.3-C.sub.10
cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkyl group, a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted
C.sub.1-C.sub.10 heterocycloalkenyl group, a substituted or
unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or
unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or
unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or
unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or
unsubstituted monovalent non-aromatic condensed polycyclic group,
--Si(Q.sub.1)(Q.sub.2)(Q.sub.3), --N(Q.sub.1)(Q.sub.2),
--B(Q.sub.1)(Q.sub.2), --C(.dbd.O)(Q.sub.1),
--S(.dbd.O).sub.2(Q.sub.1), and --P(.dbd.O)(Q.sub.1)(Q.sub.2),
[0030] R.sub.21 to R.sub.24, R.sub.27, and R.sub.28 may each
independently be selected from hydrogen, deuterium, --F, --Cl,
--Br, --I, a hydroxyl group, a cyano group, a nitro group, an
amidino group, a hydrazino group, a hydrazono group, a substituted
or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or
unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or
unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or
unsubstituted C.sub.1-C.sub.60 alkoxy group, a substituted or
unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or
unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a
substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a
substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl
group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group,
a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a
substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a
substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a
substituted or unsubstituted monovalent non-aromatic condensed
polycyclic group, a substituted or unsubstituted monovalent
non-aromatic condensed heteropolycyclic group,
--Si(Q.sub.4)(Q.sub.5)(Q.sub.6), --N(Q.sub.4)(Q.sub.5),
--B(Q.sub.4)(Q.sub.5), --C(.dbd.O)(Q.sub.4),
--S(.dbd.O).sub.2(Q.sub.4), and --P(.dbd.O)(Q.sub.4)(Q.sub.5),
[0031] b1 to b9, b21, and b22 may each independently be an integer
selected from 1 to 3,
[0032] c1, c2, and c5 to c7 may each independently be an integer
selected from 0 to 10, provided that the sum of c5, c6, and c7 is 1
or more,
[0033] c8 and c9 may each independently be an integer selected from
0 to 4, provided that the sum of c8 and c9 is 1 or more,
[0034] at least one substituent of the substituted C.sub.3-C.sub.10
cycloalkylene group, substituted C.sub.1-C.sub.10
heterocycloalkylene group, substituted C.sub.3-C.sub.10
cycloalkenylene group, substituted C.sub.1-C.sub.10
heterocycloalkenylene group, substituted C.sub.6-C.sub.60 arylene
group, substituted C.sub.1-C.sub.60 heteroarylene group, a
substituted divalent non-aromatic condensed polycyclic group, a
substituted divalent non-aromatic condensed heteropolycyclic group,
substituted C.sub.1-C.sub.60 alkyl group, substituted
C.sub.2-C.sub.60 alkenyl group, substituted C.sub.2-C.sub.60
alkynyl group, substituted C.sub.1-C.sub.60 alkoxy group,
substituted C.sub.3-C.sub.10 cycloalkyl group, substituted
C.sub.1-C.sub.10 heterocycloalkyl group, substituted
C.sub.3-C.sub.10 cycloalkenyl group, substituted C.sub.1-C.sub.10
heterocycloalkenyl group, substituted C.sub.6-C.sub.60 aryl group,
substituted C.sub.6-C.sub.60 aryloxy group, substituted
C.sub.6-C.sub.60 arylthio group, substituted C.sub.1-C.sub.60
heteroaryl group, substituted monovalent non-aromatic condensed
polycyclic group, and substituted monovalent non-aromatic condensed
heteropolycyclic group may be selected from the group consisting
of:
[0035] deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a cyano
group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60
alkenyl group, a C.sub.2-C.sub.60 alkynyl group, and a
C.sub.1-C.sub.60 alkoxy group;
[0036] a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl
group, a C.sub.2-C.sub.60 alkynyl group, and a C.sub.1-C.sub.60
alkoxy group, each substituted with at least one selected from
deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a cyano group, a
nitro group, an amidino group, a hydrazino group, a hydrazono
group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60
arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, a monovalent non-aromatic
condensed heteropolycyclic group,
--Si(Q.sub.11)(Q.sub.12)(Q.sub.13), --N(Q.sub.11)(Q.sub.12),
--B(Q.sub.11)(Q.sub.12), --C(.dbd.O)(Q.sub.11),
--S(.dbd.O).sub.2(Q.sub.11), and
--P(.dbd.O)(Q.sub.11)(Q.sub.12);
[0037] a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60
arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, a monovalent non-aromatic
condensed heteropolycyclic group, a biphenyl group, and a terphenyl
group;
[0038] a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60
arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, and a monovalent
non-aromatic condensed heteropolycyclic group, each substituted
with at least one selected from deuterium, --F, --Cl, --Br, --I, a
hydroxyl group, a cyano group, a nitro group, an amidino group, a
hydrazino group, a hydrazono group, a C.sub.1-C.sub.60 alkyl group,
a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group,
a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl
group, a C.sub.1-C.sub.10 heterocycloalkyl group, a
C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10
heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a
C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group,
a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic
condensed polycyclic group, a monovalent non-aromatic condensed
heteropolycyclic group, --Si(Q.sub.21)(Q.sub.22)(Q.sub.23),
--N(Q.sub.21)(Q.sub.22), --B(Q.sub.21)(Q.sub.22),
--C(.dbd.O)(Q.sub.21), --S(.dbd.O).sub.2(Q.sub.21), and
--P(.dbd.O)(Q.sub.21)(Q.sub.22); and
[0039] --Si(Q.sub.31)(Q.sub.32)(Q.sub.33), --N(Q.sub.31)(Q.sub.32),
--B(Q.sub.31)(Q.sub.32), --C(.dbd.O)(Q.sub.31),
--S(.dbd.O).sub.2(Q.sub.31), and
--P(.dbd.O)(Q.sub.31)(Q.sub.32),
[0040] wherein Q.sub.1 to Q.sub.6, Q.sub.11 to Q.sub.13, Q.sub.21
to Q.sub.23, and Q.sub.31 to Q.sub.33 may each independently be
selected from hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl
group, a cyano group, a nitro group, an amidino group, a hydrazino
group, a hydrazono group, a C.sub.1-C.sub.60 alkyl group, a
C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a
C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group,
a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10
cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a
C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryl group
substituted with a C.sub.1-C.sub.60 alkyl group, a C.sub.6-C.sub.60
aryl group substituted with a C.sub.6-C.sub.60 aryl group, a
terphenyl group, a C.sub.1-C.sub.60 heteroaryl group, a
C.sub.1-C.sub.60 heteroaryl group substituted with a
C.sub.1-C.sub.60 alkyl group, a C.sub.1-C.sub.60 heteroaryl group
substituted with a C.sub.6-C.sub.60 aryl group, a monovalent
non-aromatic condensed polycyclic group, and a monovalent
non-aromatic condensed heteropolycyclic group.
BRIEF DESCRIPTION OF THE DRAWINGS
[0041] These and/or other aspects will become apparent and more
readily appreciated from the following description of the example
embodiments, taken in conjunction with the accompanying drawings,
in which:
[0042] FIG. 1 is a schematic view of an organic light-emitting
device according to an embodiment of the present disclosure;
[0043] FIG. 2 is a schematic view of an organic light-emitting
device according to an embodiment of the present disclosure;
[0044] FIG. 3 is a schematic view of an organic light-emitting
device according to an embodiment of the present disclosure;
[0045] FIG. 4 is a schematic view of an organic light-emitting
device according to an embodiment of the present disclosure;
and
[0046] FIG. 5 is a schematic view of an organic light-emitting
device according to an embodiment of the present disclosure.
DETAILED DESCRIPTION
[0047] Reference will now be made in more detail to example
embodiments, examples of which are illustrated in the accompanying
drawings, wherein like reference numerals refer to like elements
throughout and duplicative descriptions thereof may not be
provided. In this regard, the present embodiments may have
different forms and should not be construed as being limited to the
descriptions set forth herein. Accordingly, the embodiments are
merely described below, by referring to the drawings, to explain
aspects of the present description. As used herein, the term
"and/or" includes any and all combinations of one or more of the
associated listed items. Expressions such as "at least one of",
"one of", and "selected from", when preceding a list of elements,
modify the entire list of elements and do not modify the individual
elements of the list.
[0048] The thicknesses of layers, films, panels, regions, etc., may
be exaggerated in the drawings for clarity. It will be understood
that when an element such as a layer, film, region, or substrate is
referred to as being "on" another element, it can be directly on
the other element or intervening element(s) may also be present. In
contrast, when an element is referred to as being "directly on"
another element, no intervening elements are present.
[0049] An organic light-emitting device according to an embodiment
of the present disclosure includes a first electrode; a second
electrode facing the first electrode; an emission layer between the
first electrode and the second electrode; a hole transport region
between the first electrode and the emission layer; and an electron
transport region between the emission layer and the second
electrode, wherein the emission layer may include a first compound,
and at least one selected from the hole transport region and the
electron transport region may include a second compound.
[0050] The first compound may be represented by one selected from
Formulae 1A to 1E, and the second compound may be represented by
Formula 2A or 2B:
##STR00003##
[0051] In Formulae 1A to 1D,
[0052] rings A.sub.11 to A.sub.13 may each independently be
selected from a C.sub.6-C.sub.60 aromatic group, a C.sub.1-C.sub.60
heteroaromatic group, and a C.sub.6-C.sub.60 non-aromatic condensed
polycyclic group.
[0053] Rings A.sub.11 and A.sub.12 in Formula 1A may each be fused
with a central 6-membered ring that includes X.sub.11 and X.sub.12
as ring-forming atoms.
[0054] Rings A.sub.11 and A.sub.12 in Formula 1B may each be fused
with a central 5-membered ring.
[0055] Rings A.sub.11 to A.sub.13 in Formula 1C may each be fused
with a central 6-membered ring.
[0056] Rings A.sub.11 to A.sub.13 in Formula 1D may each be fused
with a central 5-membered ring.
[0057] For example, rings A.sub.11 to A.sub.13 in Formula 1A to 1D
may each independently be selected from a benzene group, a
naphthalene group, an anthracene group, a phenanthrene group, a
pyrene group, a triphenylene group, an indene group, a fluorene
group, a benzofluorene group, a spiro-bifluorene group, a pyridine
group, a pyrazine group, a pyrimidine group, a pyridazine group, a
pyrrole group, an imidazole group, a quinoline group, an
isoquinoline group, a quinoxaline group, a quinazoline group, a
triazine group, an indenopyrazine group, an indenopyridine group, a
phenanthroline group, and a phenanthridine group.
[0058] In one or more embodiments, rings A.sub.11 to A.sub.13 in
Formulae 1A to 1D may each independently be selected from a benzene
group, a naphthalene group, a phenanthrene group, a triphenylene
group, a pyridine group, a pyridazine group, a pyrimidine group, a
pyrazine group, an indenopyrazine group, an indenopyridine group, a
fluorene group, and an indene group, but embodiments of the present
disclosure are not limited thereto.
[0059] Rings A.sub.21, A.sub.22, and A.sub.23 in Formulae 2A and 2B
may each independently be selected from a C.sub.5-C.sub.60
carbocyclic group and a C.sub.1-C.sub.60 heterocyclic group, each
substituted with at least one
*-[(L.sub.22).sub.a22-(R.sub.22).sub.b22]. L.sub.22, a22, R.sub.22,
and b22 will be described in detail below.
[0060] Each T.sub.11 and each T.sub.12 in Formulae 2A and 2B may
independently be selected from carbon (C) and nitrogen (N), two or
more of the three T.sub.11(s) in Formula 2A may be identical to or
different from each other, T.sub.13 may be N or C(R.sub.27),
T.sub.14 may be N or C(R.sub.28), two or more of the three
T.sub.12(s) in Formula 2A may be identical to or different from
each other, the two T.sub.11(s) in Formula 2B may be identical to
or different from each other, the two T.sub.12(s) in Formula 2B may
be identical to or different from each other, and each bond between
T.sub.11 and T.sub.12 may be a single bond or a double bond;
wherein the three T.sub.11(s) and the three T.sub.12(s) in Formula
2A are not all nitrogen, and the two T.sub.11(s), the two
T.sub.12(S), T.sub.13, and T.sub.14 in Formula 2B are not all
nitrogen. Rings A.sub.21, A.sub.22, and A.sub.23 may each be
condensed (e.g., fused) with a central 7-membered ring in Formulae
2A and 2B, such that they each share a T.sub.11 and a T.sub.12 with
the central 7-membered ring.
[0061] Each *-[(L.sub.22).sub.a22-(R.sub.22).sub.b22] in ring
A.sub.21, *-[(L.sub.22).sub.a22-(R.sub.22).sub.b22] in ring
A.sub.22, and *-[(L.sub.22).sub.a22-(R.sub.22).sub.b22] in ring
A.sub.23 may be identical to or different from each other.
[0062] In one or more embodiments, when the number of
*-[(L.sub.22).sub.a22-(R.sub.22).sub.b22](s) in ring A.sub.21 is
two or more, the two or more
*-[(L.sub.22).sub.a22-(R.sub.22).sub.b22](s) may be identical to or
different from each other; when the number of
*-[(L.sub.22).sub.a22-(R.sub.22).sub.b22](s) in ring A.sub.22 is
two or more, the two or more
*-[(L.sub.22).sub.a22-(R.sub.22).sub.b22](s) may be identical to or
different from each other; and when the number of
*-[(L.sub.22).sub.a22-(R.sub.22).sub.b22](s) in ring A.sub.23 is
two or more, the two or more
*-[(L.sub.22).sub.a22-(R.sub.22).sub.b22](s) may be identical to or
different from each other.
[0063] In one embodiment, rings A.sub.21, A.sub.22, and A.sub.23 in
Formulae 2A and 2B may each independently be selected from a
benzene group, a naphthalene group, an anthracene group, an indene
group, a fluorene group, a pyridine group, a pyrimidine group, a
pyrazine group, a pyridazine group, a quinoline group, an
isoquinoline group, a pyrrole group, a pyrazole group, an imidazole
group, an oxazole group, a thiazole group, a cyclopentadiene group,
a silole group, a selenophene group, a furan group, a thiophene
group, an indole group, a benzimidazole group, a benzoxazole group,
a benzothiazole group, an indene group, a benzosilole group, a
benzoselenophene group, a benzofuran group, a benzothiophene group,
a carbazole group, a fluorene group, a dibenzosilole group, a
dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene
group, a pyrrolopyridine group, a cyclopentapyridine group, a
silolopyridine group, a selenophenopyridine group, a furopyridine
group, a thienopyridine group, a pyrrolopyrimidine group, a
cyclopentapyrimidine group, a silolopyrimidine group, a
selenophenopyrimidine group, a furopyrimidine group, a
thienopyrimidine group, a pyrrolopyrazine group, a
cyclopentapyrazine group, a silolopyrazine group, a
selenophenopyrazine group, a furopyrazine group, a thienopyrazine
group, a naphthopyrrole group, a cyclopentanaphthalene group, a
naphthosilole group, a naphthoselenothiophene group, a naphthofuran
group, a naphthothiophene group, a pyrroloquinoline group, a
cyclopentaquinoline group, a siloloquinoline group, a
selenophenoquinoline group, a furoquinoline group, a
thienoquinoline group, a pyrroloisoquinoline group, a
cyclopentaisoquinoline group, a siloloisoquinoline group, a
selenophenoisoquinoline group, a furoisoquinoline group, a
thienoisoquinoline group, an azacarbazole group, an azafluorene
group, an azadibenzosilole group, an azadibenzoselenophene group,
an azadibenzofuran group, an azadibenzothiophene group, an
indenoquinoline group, an indenoisoquinoline group, an
indenoquinoxaline group, a phenanthroline group, and an
naphthoindole group, each substituted with at least one
*-[(L.sub.22).sub.a22-(R.sub.22).sub.b22].
[0064] In one or more embodiments, the case in which rings
A.sub.21, A.sub.22, and A.sub.23 in the second compound represented
by Formula 2A or 2B are all (e.g., simultaneously) benzene groups,
each substituted with at least one
*-[(L.sub.22).sub.a22-(R.sub.22).sub.b22], is excluded.
[0065] In one or more embodiments, rings A.sub.21, A.sub.22, and
A.sub.23 in Formulae 2A and 2B may each independently be selected
from groups represented by Formulae 2-1 to 2-36, each substituted
with at least one *-[(L.sub.22).sub.a22-(R.sub.22).sub.b22]:
##STR00004## ##STR00005## ##STR00006## ##STR00007##
##STR00008##
[0066] In Formulae 2-1 to 2-36,
[0067] T.sub.11 and T.sub.12 may each independently be the same as
described herein in connection with Formulae 2A and 2B,
[0068] X.sub.22 and X.sub.23 may each independently be selected
from oxygen (O), sulfur (S), selenium (Se), a moiety including C, a
moiety including N, and a moiety including Si,
[0069] T.sub.21 to T.sub.28 may each independently be selected from
N and a moiety including C.
[0070] When rings A.sub.21 to A.sub.23 include both X.sub.22 and
X.sub.23, X.sub.22 and X.sub.23 may be identical to or different
from each other.
[0071] For example, in Formulae 2-1 to 2-36, X.sub.22 and X.sub.23
may each independently be selected from O, S, Se,
C(R.sub.25)(R.sub.26), N-[(L.sub.22).sub.a22-(R.sub.22).sub.b22],
and Si(R.sub.25)(R.sub.26), and T.sub.21 to T.sub.28 may each
independently be selected from N and
C-[(L.sub.22).sub.a22-(R.sub.22).sub.b22]. R.sub.25 and R.sub.26
may each independently be selected from groups represented by
*-[(L.sub.22).sub.a22-(R.sub.22).sub.b22)].
[0072] For example, X.sub.22 and X.sub.23 in Formulae 2-1 to 2-36
may each independently be selected from O, S, Se,
C(R.sub.25)(R.sub.26), N-[(L.sub.22).sub.a22-(R.sub.22).sub.b22],
and Si(R.sub.25)(R.sub.26), and T.sub.21 to T.sub.28 may each
independently be selected from N and
C-[(L.sub.22).sub.a22-(R.sub.22).sub.b22]. R.sub.25 and R.sub.26
may each independently be selected from groups represented by
*-[(L.sub.22).sub.a22-(R.sub.22).sub.b22)].
[0073] In one or more embodiments, rings A.sub.21, A.sub.22, and
A.sub.23 in Formulae 2A and 2B may each independently be selected
from groups represented by Formulae 2-101 to 2-229:
##STR00009## ##STR00010## ##STR00011## ##STR00012## ##STR00013##
##STR00014## ##STR00015## ##STR00016## ##STR00017## ##STR00018##
##STR00019## ##STR00020## ##STR00021## ##STR00022## ##STR00023##
##STR00024## ##STR00025## ##STR00026## ##STR00027##
##STR00028##
[0074] In Formulae 2-101 to 2-229,
[0075] T.sub.11 and T.sub.12 may each independently be the same as
described above,
[0076] X.sub.22 and X.sub.23 may each independently be the same as
described above, and
[0077] R.sub.31 to R.sub.38 may each independently be selected from
substituents represented by
*-[(L.sub.22).sub.a22-(R.sub.22).sub.b22].
[0078] When the number of
*-[(L.sub.22).sub.a22-(R.sub.22).sub.b22](s) in R.sub.31 to
R.sub.38 is 2 or more, the 2 or more
*-[(L.sub.22).sub.a22-(R.sub.22).sub.b22](s) may be identical to or
different from each other.
[0079] In one or more embodiments, the case in which rings
A.sub.21, A.sub.22, and A.sub.23 in Formulae 2A and 2B are all
(e.g., simultaneously) represented by Formula 2-104 is
excluded.
[0080] In one or more embodiments, the second compound represented
by Formula 2A or 2B may be represented by one selected from
Formulae 2-201A to 2-269A (denoting a formula based on Formula 2A),
and rings A.sub.21, A.sub.22, and A.sub.23 in Formulae 2-201A to
2-269A may each be selected from the formulae shown in Table 1:
TABLE-US-00001 TABLE 1 Formula No. of ring Formula No. of ring
Formula No. of ring Formula No. A.sub.21 A.sub.22 A.sub.23 2-201A
2-2 2-4 2-4 2-202A 2-4 2-4 2-1 2-203A 2-4 2-4 2-2 2-204A 2-4 2-4
2-3 2-205A 2-4 2-1 2-4 2-206A 2-4 2-2 2-4 2-207A 2-4 2-4 2-10
2-208A 2-11 2-4 2-4 2-209A 2-4 2-4 2-11 2-210A 2-4 2-10 2-4 2-211A
2-4 2-4 2-8 2-212A 2-4 2-9 2-4 2-213A 2-4 2-4 2-14 2-214A 2-17 2-4
2-4 2-215A 2-4 2-4 2-15 2-216A 2-13 2-4 2-4 2-217A 2-4 2-4 2-16
2-218A 2-4 2-4 2-13 2-219A 2-16 2-4 2-4 2-220A 2-4 2-4 2-12 2-221A
2-4 2-4 2-17 2-222A 2-4 2-16 2-4 2-223A 2-4 2-15 2-4 2-224A 2-4
2-14 2-4 2-225A 2-4 2-17 2-4 2-226A 2-19 2-4 2-4 2-227A 2-22 2-4
2-4 2-228A 2-18 2-4 2-4 2-229A 2-23 2-4 2-4 2-230A 2-21 2-4 2-4
2-231A 2-20 2-4 2-4 2-232A 2-4 2-23 2-4 2-233A 2-4 2-18 2-4 2-234A
2-4 2-21 2-4 2-235A 2-4 2-19 2-4 2-236A 2-5 2-2 2-4 2-237A 2-5 2-1
2-4 2-238A 2-2 2-2 2-4 2-239A 2-4 2-23 2-1 2-240A 2-6 2-10 2-4
2-241A 2-4 2-4 2-29 2-242A 2-7 2-4 2-10 2-243A 2-11 2-4 2-10 2-244A
2-4 2-10 2-6 2-245A 2-11 2-11 2-4 2-246A 2-11 2-11 2-5 2-247A 2-11
2-11 2-10 2-248A 2-7 2-9 2-4 2-249A 2-4 2-4 2-25 2-250A 2-11 2-15
2-4 2-251A 2-18 2-28 2-4 2-252A 2-23 2-10 2-4 2-253A 2-4 2-27 2-4
2-254A 2-6 2-18 2-4 2-255A 2-4 2-23 2-5 2-256A 2-23 2-4 2-14 2-257A
2-17 2-4 2-14 2-258A 2-14 2-4 2-12 2-259A 2-17 2-4 2-12 2-260A 2-14
2-16 2-2 2-261A 2-17 2-5 2-14 2-262A 2-17 2-13 2-17 2-263A 2-17
2-14 2-12 2-264A 2-17 2-12 2-12 2-265A 2-5 2-1 2-18 2-266A 2-4 2-29
2-4 2-267A 2-4 2-31 2-4 2-268A 2-4 2-33 2-4 2-269A 2-4 2-35 2-4
[0081] In one or more embodiments, the second compound represented
by Formula 2A or 2B may be represented by one selected from
Formulae 2-201B to 2-215B (denoting a formula based on Formula 2B),
and rings A.sub.21 and A.sub.23 in Formulae 2-201B to 2-215B may
each be selected from the formulae shown in Table 2:
TABLE-US-00002 TABLE 2 Formula Formula No. of Formula No. of ring
Formula No. No. of ring A.sub.21 ring A.sub.22 A.sub.23 2-201B 2-4
-- 2-19 2-202B 2-4 -- 2-22 2-203B 2-4 -- 2-18 2-204B 2-4 -- 2-23
2-205B 2-4 -- 2-21 2-206B 2-4 -- 2-20 2-207B 2-5 -- 2-23 2-208B 2-7
-- 2-23 2-209B 2-4 -- 2-26 2-210B 2-7 -- 2-22 2-211B 2-13 -- 2-16
2-212B 2-5 -- 2-19 2-213B 2-7 -- 2-20 2-214B 2-19 -- 2-18 2-215B
2-18 -- 2-18
[0082] In one or more embodiments, the second compound represented
by Formula 2A or 2B may be represented by one selected from
Formulae 2-301A to 2-421A (denoting a formula based on Formula 2A),
and rings A.sub.21, A.sub.22, and A.sub.23 in Formulae 2-301A to
2-419A and 2-421A to 2-431A may each be selected from the formulae
shown in Table 3:
TABLE-US-00003 TABLE 3 Formula No. of ring Formula No. of ring
Formula No. of ring Formula No. A.sub.21 A.sub.22 A.sub.23 2-301A
2-104 2-147 2-104 2-302A 2-102 2-104 2-104 2-303A 2-104 2-104 2-101
2-304A 2-104 2-104 2-102 2-305A 2-104 2-104 2-103 2-306A 2-104
2-101 2-104 2-307A 2-104 2-102 2-104 2-308A 2-104 2-104 2-147
2-309A 2-157 2-104 2-104 2-310A 2-104 2-104 2-157 2-311A 2-104
2-147 2-107 2-312A 2-104 2-149 2-104 2-313A 2-104 2-156 2-104
2-314A 2-107 2-147 2-106 2-315A 2-104 2-151 2-104 2-316A 2-104
2-147 2-106 2-317A 2-104 2-148 2-104 2-318A 2-104 2-150 2-104
2-319A 2-106 2-147 2-104 2-320A 2-104 2-106 2-147 2-321A 2-157
2-107 2-104 2-322A 2-106 2-104 2-147 2-323A 2-104 2-107 2-147
2-324A 2-107 2-104 2-147 2-325A 2-104 2-104 2-160 2-326A 2-104
2-111 2-157 2-327A 2-108 2-104 2-158 2-328A 2-111 2-104 2-157
2-329A 2-107 2-147 2-104 2-330A 2-104 2-104 2-135 2-331A 2-104
2-141 2-104 2-332A 2-104 2-142 2-104 2-333A 2-107 2-104 2-135
2-334A 2-104 2-111 2-135 2-335A 2-104 2-143 2-104 2-336A 2-106
2-142 2-104 2-337A 2-107 2-142 2-106 2-338A 2-104 2-104 2-169
2-339A 2-184 2-104 2-104 2-340A 2-104 2-104 2-182 2-341A 2-168
2-104 2-104 2-342A 2-104 2-104 2-183 2-343A 2-104 2-104 2-168
2-344A 2-183 2-104 2-104 2-345A 2-104 2-104 2-167 2-346A 2-104
2-104 2-184 2-347A 2-104 2-183 2-104 2-348A 2-104 2-182 2-104
2-349A 2-104 2-169 2-104 2-350A 2-104 2-184 2-104 2-351A 2-107
2-104 2-179 2-352A 2-111 2-104 2-169 2-353A 2-104 2-111 2-182
2-354A 2-106 2-104 2-185 2-355A 2-171 2-104 2-104 2-356A 2-104
2-104 2-115 2-357A 2-104 2-104 2-178 2-358A 2-104 2-106 2-167
2-359A 2-108 2-105 2-167 2-360A 2-105 2-104 2-167 2-361A 2-112
2-104 2-184 2-362A 2-104 2-192 2-104 2-363A 2-107 2-182 2-106
2-364A 2-104 2-169 2-105 2-365A 2-105 2-184 2-104 2-366A 2-105
2-169 2-105 2-367A 2-198 2-104 2-104 2-368A 2-201 2-104 2-104
2-369A 2-197 2-104 2-104 2-370A 2-202 2-104 2-104 2-371A 2-200
2-104 2-104 2-372A 2-199 2-104 2-104 2-373A 2-104 2-202 2-104
2-374A 2-104 2-197 2-104 2-375A 2-104 2-200 2-104 2-376A 2-104
2-198 2-104 2-377A 2-209 2-104 2-104 2-378A 2-207 2-104 2-104
2-379A 2-200 2-106 2-104 2-380A 2-104 2-208 2-104 2-381A 2-105
2-198 2-108 2-382A 2-202 2-102 2-104 2-383A 2-202 2-101 2-106
2-384A 2-102 2-102 2-107 2-385A 2-104 2-202 2-101 2-386A 2-123
2-147 2-104 2-387A 2-104 2-104 2-218 2-388A 2-116 2-104 2-147
2-389A 2-157 2-104 2-147 2-390A 2-107 2-147 2-115 2-391A 2-157
2-157 2-104 2-392A 2-157 2-157 2-114 2-393A 2-157 2-157 2-147
2-394A 2-116 2-147 2-104 2-395A 2-104 2-104 2-210 2-396A 2-157
2-182 2-104 2-397A 2-197 2-213 2-104 2-398A 2-202 2-167 2-104
2-399A 2-104 2-216 2-104 2-400A 2-124 2-197 2-104 2-401A 2-104
2-202 2-114 2-402A 2-168 2-104 2-169 2-403A 2-184 2-104 2-169
2-404A 2-169 2-104 2-167 2-405A 2-184 2-106 2-167 2-406A 2-169
2-183 2-102 2-407A 2-184 2-114 2-169 2-408A 2-184 2-168 2-184
2-409A 2-184 2-104 2-167 2-410A 2-184 2-167 2-167 2-411A 2-114
2-101 2-197 2-412A 2-104 2-149 2-104 2-413A 2-106 2-104 2-147
2-414A 2-104 2-104 2-168 2-415A 2-200 2-106 2-104 2-416A 2-104
2-104 2-183 2-417A 2-104 2-104 2-101 2-418A 2-105 2-169 2-105
2-419A 2-104 2-147 2-107 2-421A 2-104 2-218 2-104 2-422A 2-104
2-226 2-104 2-423A 2-104 2-222 2-104 2-424A 2-104 2-228 2-104
2-425A 2-104 2-151 2-104 2-426A 2-106 2-147 2-107 2-427A 2-104
2-147 2-106 2-428A 2-107 2-150 2-104 2-429A 2-104 2-143 2-104
2-430A 2-107 2-142 2-106 2-431A 2-104 2-142 2-104
[0083] In one or more embodiments, the second compound represented
by Formula 2A or 2B may be represented by one selected from
Formulae 2-301B to 2-320B (denoting a formula based on Formula 2B),
and rings A.sub.21 and A.sub.23 in Formulae 2-301B to 2-320B may
each be selected from the formulae shown in Table 4:
TABLE-US-00004 TABLE 4 Formula No. of ring Formula No. of ring
Formula No. of ring Formula No. A.sub.21 A.sub.22 A.sub.23 2-301B
2-104 -- 2-198 2-302B 2-104 -- 2-201 2-303B 2-104 -- 2-197 2-304B
2-104 -- 2-202 2-305B 2-104 -- 2-200 2-306B 2-104 -- 2-199 2-307B
2-104 -- 2-203 2-308B 2-104 -- 2-204 2-309B 2-106 -- 2-205 2-310B
2-104 -- 2-206 2-311B 2-112 -- 2-199 2-312B 2-114 -- 2-202 2-313B
2-116 -- 2-202 2-314B 2-104 -- 2-214 2-315B 2-130 -- 2-201 2-316B
2-168 -- 2-183 2-317B 2-114 -- 2-198 2-318B 2-116 -- 2-199 2-319B
2-198 -- 2-197 2-320B 2-197 -- 2-197
[0084] In Formula 1A, X.sub.11 may be N or
C[(L.sub.3).sub.a3-(R.sub.3).sub.b3], and X.sub.12 may be N or
C[(L.sub.4).sub.a4-(R.sub.4).sub.b4].
[0085] For example, in Formula 1A,
[0086] X.sub.11 may be N, and X.sub.12 may be
C[(L.sub.4).sub.a4-(R.sub.4).sub.b4],
[0087] X.sub.11 may be C[(L.sub.3).sub.a3-(R.sub.3).sub.b3], and
X.sub.12 may be N, or
[0088] X.sub.11 may be C[(L.sub.3).sub.a3-(R.sub.3).sub.b3], and
X.sub.12 may be C[(L.sub.4).sub.a4-(R.sub.4).sub.b4], but
embodiments of X.sub.11 are not limited thereto.
[0089] X.sub.21 in Formulae 2A and 2B may be selected from O, S,
Se, C(R.sub.23)(R.sub.24), Si(R.sub.23)(R.sub.24), and
N-[(L.sub.21).sub.a21-(R.sub.21).sub.b21].
[0090] In one embodiment, X.sub.21 in Formulae 2A and 2B may be
N[(L.sub.21).sub.a21-(R.sub.21).sub.b21].
[0091] In one or more embodiments, X.sub.21 in Formulae 2A and 2B
may be O, S, Se, C(R.sub.23)(R.sub.24), or
Si(R.sub.23)(R.sub.24),
[0092] at least one selected from rings A.sub.21, A.sub.22, and
A.sub.23 in Formula 2A and at least one selected from rings
A.sub.21 and A.sub.23 in Formula 2B may each independently be
selected from groups represented by Formulae 2-1 to 2-3, 2-10 to
2-27, and 2-33 to 2-36, and X.sub.22 or X.sub.23 in Formulae 2-1 to
2-3, 2-10 to 2-27, and 2-33 to 2-36 may be
N-[(L.sub.22).sub.a22-(R.sub.22).sub.b22].
[0093] In one or more embodiments, X.sub.21 in Formulae 2A and 2B
may be O, S, Se, C(R.sub.23)(R.sub.24), or
Si(R.sub.23)(R.sub.24),
[0094] at least one selected from rings A.sub.21, A.sub.22, and
A.sub.23 in Formula 2A and at least one selected from rings
A.sub.21 and A.sub.23 in Formula 2B may each independently be
selected from groups represented by Formulae 2-101 to 2-103, 2-147
to 2-211, 2-214 to 2-219, and 2-226 to 2-229, and X.sub.22 or
X.sub.23 in Formula 2-101 to 2-103, 2-147 to 2-211, 2-214 to 2-219,
and 2-226 to 2-229 may be
N-[(L.sub.22).sub.a22-(R.sub.22).sub.b22], but embodiments of the
present disclosure are not limited thereto.
[0095] In Formulae 2A and 2B, X.sub.21 may be O, S, Se,
C(R.sub.23)(R.sub.24), Si(R.sub.23)(R.sub.24), or
N-[(L.sub.21).sub.a21-(R.sub.21).sub.b21], and X.sub.22 and
X.sub.23 may each independently be O, S, Se, C(R.sub.25)(R.sub.26),
Si(R.sub.25)(R.sub.26), or
N-[(L.sub.22).sub.a22-(R.sub.22).sub.b22]. L.sub.21, L.sub.22, a21,
a22, R.sub.21 to R.sub.26, b21, and b22 may each independently be
the same as described below.
[0096] L.sub.1 to L.sub.9 in Formulae 1A to 1E, 2A, and 2B may each
independently be selected from a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkylene group, a substituted or
unsubstituted C.sub.1-C.sub.10 heterocycloalkylene group, a
substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenylene
group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkenylene group, a substituted or unsubstituted
C.sub.6-C.sub.60 arylene group, a substituted or unsubstituted
C.sub.1-C.sub.60 heteroarylene group, and a substituted or
unsubstituted divalent non-aromatic condensed polycyclic group,
[0097] L.sub.21 and L.sub.22 may each independently be selected
from a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkylene
group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkylene group, a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkenylene group, a substituted or
unsubstituted C.sub.1-C.sub.10 heterocycloalkenylene group, a
substituted or unsubstituted C.sub.6-C.sub.60 arylene group, a
substituted or unsubstituted C.sub.1-C.sub.60 heteroarylene group,
a substituted or unsubstituted divalent non-aromatic condensed
polycyclic group, and a substituted or unsubstituted divalent
non-aromatic condensed heteropolycyclic group.
[0098] For example,
[0099] in Formulae 1A to 1E, 2A, and 2B,
[0100] L.sub.1 to L.sub.9, L.sub.21, and L.sub.22 may each
independently be selected from the group consisting of:
[0101] a phenylene group, a pentalenylene group, an indenylene
group, a naphthylene group, an azulenylene group, a heptalenylene
group, an indacenylene group, an acenaphthylene group, a
fluorenylene group, a spiro-bifluorenylene group, a
spiro-benzofluorene-fluorenylene group, a benzofluorenylene group,
a dibenzofluorenylene group, a phenalenylene group, a
phenanthrenylene group, an anthracenylene group, a fluoranthenylene
group, a triphenylenylene group, a pyrenylene group, a chrysenylene
group, a naphthacenylene group, a picenylene group, a perylenylene
group, a pentaphenylene group, a hexacenylene group, a
pentacenylene group, a rubicenylene group, a coronenylene group, an
ovalenylene group, a pyrrolylene group, a thiophenylene group, a
furanylene group, a silolylene group, an imidazolylene group, a
pyrazolylene group, a thiazolylene group, an isothiazolylene group,
an oxazolylene group, an isoxazolylene group, a pyridinylene group,
a pyrazinylene group, a pyrimidinylene group, a pyridazinylene
group, an indolylene group, an isoindolylene group, an indazolylene
group, a purinylene group, a quinolinylene group, an
isoquinolinylene group, a benzoquinolinylene group, a
phthalazinylene group, a naphthyridinylene group, a quinoxalinylene
group, a quinazolinylene group, a cinnolinylene group, a
phenanthridinylene group, an acridinylene group, a
phenanthrolinylene group, a phenazinylene group, a
benzimidazolylene group, a benzofuranylene group, a
benzothiophenylene group, a benzosilolylene group, an
isobenzothiazolylene group, a benzoxazolylene group, an
isobenzoxazolylene group, a triazolylene group, a tetrazolylene
group, an oxadiazolylene group, a triazinylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
dibenzosilolylene group, a carbazolylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, a
thiadiazolylene group, an imidazopyridinylene group, an
imidazopyrimidinylene group, an oxazolopyridinylene group, a
thiazolopyridinylene group, a benzonaphthyridinylene group, an
azafluorenylene group, an azaspiro-bifluorenylene group, an
azacarbazolylene group, an azadibenzofuranylene group, an
azadibenzothiophenylene group, and an azadibenzosilolylene group;
and
[0102] a phenylene group, a pentalenylene group, an indenylene
group, a naphthylene group, an azulenylene group, a heptalenylene
group, an indacenylene group, an acenaphthylene group, a
fluorenylene group, a spiro-bifluorenylene group, a
spiro-benzofluorene-fluorenylene group, a benzofluorenylene group,
a dibenzofluorenylene group, a phenalenylene group, a
phenanthrenylene group, an anthracenylene group, a fluoranthenylene
group, a triphenylenylene group, a pyrenylene group, a chrysenylene
group, a naphthacenylene group, a picenylene group, a perylenylene
group, a pentaphenylene group, a hexacenylene group, a
pentacenylene group, a rubicenylene group, a coronenylene group, an
ovalenylene group, a pyrrolylene group, a thiophenylene group, a
furanylene group, a silolylene group, an imidazolylene group, a
pyrazolylene group, a thiazolylene group, an isothiazolylene group,
an oxazolylene group, an isoxazolylene group, a pyridinylene group,
a pyrazinylene group, a pyrimidinylene group, a pyridazinylene
group, an indolylene group, an isoindolylene group, an indazolylene
group, a purinylene group, a quinolinylene group, an
isoquinolinylene group, a benzoquinolinylene group, a
phthalazinylene group, a naphthyridinylene group, a quinoxalinylene
group, a quinazolinylene group, a cinnolinylene group, a
phenanthridinylene group, an acridinylene group, a
phenanthrolinylene group, a phenazinylene group, a
benzimidazolylene group, a benzofuranylene group, a
benzothiophenylene group, a benzosilolylene group, an
isobenzothiazolylene group, a benzoxazolylene group, an
isobenzoxazolylene group, a triazolylene group, a tetrazolylene
group, an oxadiazolylene group, a triazinylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
dibenzosilolylene group, a carbazolylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, a
thiadiazolylene group, an imidazopyridinylene group, an
imidazopyrimidinylene group, an oxazolopyridinylene group, a
thiazolopyridinylene group, a benzonaphthyridinylene group, an
azafluorenylene group, an azaspiro-bifluorenylene group, an
azacarbazolylene group, an azadibenzofuranylene group, an
azadibenzothiophenylene group, and an azadibenzosilolylene group,
each substituted with at least one selected from deuterium, --F,
--Cl, --Br, --I, a hydroxyl group, a cyano group, a nitro group, an
amidino group, a hydrazino group, a hydrazono group, a
C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a
C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, a monovalent non-aromatic
condensed heteropolycyclic group, a biphenyl group, a terphenyl
group, --Si(Q.sub.31)(Q.sub.32)(Q.sub.33), --N(Q.sub.31)(Q.sub.32),
--B(Q.sub.31)(Q.sub.32), --C(.dbd.O)(Q.sub.31),
--S(.dbd.O).sub.2(Q.sub.31), and --P(.dbd.O)(Q.sub.31)(Q.sub.32),
and
[0103] L.sub.1 to L.sub.9 may each not be a substituted or
unsubstituted carbazolylene group, a substituted or unsubstituted
dibenzofuranylene group, a substituted or unsubstituted
dibenzothiophenylene group, a substituted or unsubstituted
dibenzosilolylene group, or a substituted or unsubstituted
dibenzocarbazolylene group,
[0104] wherein Q.sub.31 to Q.sub.33 may each independently be
selected from the group consisting of:
[0105] a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy
group, a phenyl group, a biphenyl group, a terphenyl group, a
naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl
group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl
group, and a quinazolinyl group; and
[0106] a phenyl group, a biphenyl group, a terphenyl group, a
naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl
group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl
group, and a quinazolinyl group, each substituted with at least one
selected from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10
alkoxy group, and a phenyl group.
[0107] In one or more embodiments,
[0108] L.sub.1 to L.sub.9, L.sub.21, and L.sub.22 in Formulae 1A to
1E, 2A, and 2B may each independently be selected from the group
consisting of:
[0109] a phenylene group, a pentalenylene group, an indenylene
group, a naphthylene group, an azulenylene group, a heptalenylene
group, an indacenylene group, an acenaphthylene group, a
fluorenylene group, a spiro-bifluorenylene group, a
benzofluorenylene group, a dibenzofluorenylene group, a
phenalenylene group, a phenanthrenylene group, an anthracenylene
group, a fluoranthenylene group, a triphenylenylene group, a
pyrenylene group, a chrysenylene group, a naphthacenylene group, a
picenylene group, a perylenylene group, a pentaphenylene group, a
hexacenylene group, a pentacenylene group, a rubicenylene group, a
coronenylene group, an ovalenylene group, a pyrrolylene group, a
thiophenylene group, a furanylene group, a silolylene group, an
indolylene group, an isoindolylene group, a benzofuranylene group,
a benzothiophenylene group, a benzosilolylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
dibenzosilolylene group, a carbazolylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, and a
pyridinylene group; and
[0110] a phenylene group, a pentalenylene group, an indenylene
group, a naphthylene group, an azulenylene group, a heptalenylene
group, an indacenylene group, an acenaphthylene group, a
fluorenylene group, a spiro-bifluorenylene group, a
benzofluorenylene group, a dibenzofluorenylene group, a
phenalenylene group, a phenanthrenylene group, an anthracenylene
group, a fluoranthenylene group, a triphenylenylene group, a
pyrenylene group, a chrysenylene group, a naphthacenylene group, a
picenylene group, a perylenylene group, a pentaphenylene group, a
hexacenylene group, a pentacenylene group, a rubicenylene group, a
coronenylene group, an ovalenylene group, a pyrrolylene group, a
thiophenylene group, a furanylene group, a silolylene group, an
indolylene group, an isoindolylene group, a benzofuranylene group,
a benzothiophenylene group, a benzosilolylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
dibenzosilolylene group, a carbazolylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, and a
pyridinylene group, each substituted with at least one selected
from deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a cyano
group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl
group, a heptalenyl group, an indacenyl group, an acenaphthyl
group, a fluorenyl group, a spiro-bifluorenylene group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group,
a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group,
a triphenylenyl group, a pyrenyl group, a chrysenyl group, a
naphthacenyl group, a picenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl
group, a thiophenyl group, a furanyl group, a silolyl group, an
indolyl group, an isoindolyl group, a benzofuranyl group, a
benzothiophenyl group, a benzosilolyl group, a dibenzofuranyl
group, a dibenzothiophenyl group, a dibenzosilolyl group, a
carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl
group, a pyridinyl group, --Si(Q.sub.31)(Q.sub.32)(Q.sub.33)
--N(Q.sub.31)(Q.sub.32), --B(Q.sub.31)(Q.sub.32),
--C(.dbd.O)(Q.sub.31), --S(.dbd.O).sub.2(Q.sub.31), and
--P(.dbd.O)(Q.sub.31)(Q.sub.32), and
[0111] L.sub.1 to L.sub.9 may each not be a substituted or
unsubstituted carbazolylene group, a substituted or unsubstituted
dibenzofuranylene group, a substituted or unsubstituted
dibenzothiophenylene group, a substituted or unsubstituted
dibenzosilolylene group, or a substituted or unsubstituted
dibenzocarbazolylene group,
[0112] wherein Q.sub.31 to Q.sub.33 may each independently be
selected from the group consisting of:
[0113] a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy
group, a phenyl group, a biphenyl group, a terphenyl group, a
naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl
group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl
group, and a quinazolinyl group; and
[0114] a phenyl group, a biphenyl group, a terphenyl group, a
naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl
group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl
group, and a quinazolinyl group, each substituted with at least one
selected from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10
alkoxy group, and a phenyl group.
[0115] In one or more embodiments, in Formulae 1A to 1E, 2A, and
2B, L.sub.1 to L.sub.9 may each independently be selected from
groups represented by Formulae 3-1 to 3-22 and 3-25 to 3-100,
[0116] L.sub.21 and L.sub.22 may each independently be selected
from groups Formulae 3-1 to 3-100, and
[0117] when L.sub.1 to L.sub.9 are each independently selected from
groups represented by Formulae 3-17 to 3-20, Y.sub.1 in Formulae
3-17 to 3-20 may be C(Z.sub.3)(Z.sub.4):
##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033##
##STR00034## ##STR00035## ##STR00036## ##STR00037## ##STR00038##
##STR00039## ##STR00040## ##STR00041## ##STR00042## ##STR00043##
##STR00044##
[0118] In Formulae 3-1 to 3-100,
[0119] Y.sub.1 may be O, S, C(Z.sub.3)(Z.sub.4), N(Z.sub.5), or
Si(Z.sub.6)(Z.sub.7),
[0120] Z.sub.1 to Z.sub.7 may each independently be selected from
hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a cyclopentyl group, a cyclohexyl group, a
cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a
phenyl group, a biphenyl group, a terphenyl group, a pentalenyl
group, an indenyl group, a naphthyl group, an azulenyl group, a
heptalenyl group, an indacenyl group, an acenaphthyl group, a
fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group,
a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a
picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl
group, a pentacenyl group, a rubicenyl group, a coronenyl group, an
ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl
group, a silolyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, an isothiazolyl group, an oxazolyl group, an
isoxazolyl group, a pyridinyl group, a pyrazinyl group, a
pyrimidinyl group, a pyridazinyl group, an indolyl group, an
isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl
group, an isoquinolinyl group, a benzoquinolinyl group, a
phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a
quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an
acridinyl group, a phenanthrolinyl group, a phenazinyl group, a
benzimidazolyl group, a benzofuranyl group, a benzothiophenyl
group, a benzosilolyl group, an isobenzothiazolyl group, a
benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a
tetrazolyl group, an oxadiazolyl group, a triazinyl group, a
dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl
group, a carbazolyl group, a benzocarbazolyl group, a
dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl
group, an imidazopyrimidinyl group, a benzonaphthyridinyl group, an
azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl
group, an azadibenzofuranyl group, an azadibenzothiophenyl group,
an azadibenzosilolyl group, --Si(Q.sub.31)(Q.sub.32)(Q.sub.33),
--N(Q.sub.31)(Q.sub.32), --B(Q.sub.31)(Q.sub.32),
--C(.dbd.O)(Q.sub.31), --S(.dbd.O).sub.2(Q.sub.31), and
--P(.dbd.O)(Q.sub.31)(Q.sub.32),
[0121] Q.sub.31 to Q.sub.33 may each independently be selected from
the group consisting of: a C.sub.1-C.sub.10 alkyl group, a
C.sub.1-C.sub.10 alkoxy group, a phenyl group, a biphenyl group, a
terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl
group, a pyrazinyl group, a quinolinyl group, an isoquinolinyl
group, a quinoxalinyl group, and a quinazolinyl group; and
[0122] a phenyl group, a biphenyl group, a terphenyl group, a
naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl
group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl
group, and a quinazolinyl group, each substituted with at least one
selected from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10
alkoxy group, and a phenyl group,
[0123] d2 may be an integer selected from 0 to 2,
[0124] d3 may be an integer selected from 0 to 3,
[0125] d4 may be an integer selected from 0 to 4,
[0126] d5 may be an integer selected from 0 to 5,
[0127] d6 may be an integer selected from 0 to 6,
[0128] d8 may be an integer selected from 0 to 8, and
[0129] * and *' may each independently indicate a binding site to a
neighboring atom.
[0130] a1 to a9, a21, and a22 in Formulae 1A to 1E and 2A to 2B
indicate the numbers of L.sub.1 to L.sub.9, L.sub.21, and L.sub.22
groups, respectively. a1 to a7, a21, and a22 in Formulae 1A to 1E
and 2A to 2B may each independently be an integer selected from 0
to 5. When a1 is two or more, two or more L.sub.1(s) may be
identical to or different from each other; when a2 is two or more,
two or more L.sub.2(s) may be identical to or different from each
other; when a3 is two or more, two or more L.sub.3(s) may be
identical to or different from each other; when a4 is two or more,
two or more L.sub.4(s) may be identical to or different from each
other; when a5 is two or more, two or more L.sub.5(s) may be
identical to or different from each other; when a6 is two or more,
two or more L.sub.6(s) may be identical to or different from each
other; when a7 is two or more, two or more L.sub.7(s) may be
identical to or different from each other; when a8 is two or more,
two or more L.sub.8(s) may be identical to or different from each
other; when a9 is two or more, two or more L.sub.9(s) may be
identical to or different from each other; when a21 is two or more,
two or more L.sub.21(s) may be identical to or different from each
other; and when a22 is two or more, two or more L.sub.22(s) may be
identical to or different from each other. When a1 is 0,
*-(L.sub.1).sub.a1-*' indicates a single bond; when a2 is 0,
*-(L.sub.2).sub.a2-*' indicates a single bond; when a3 is 0,
*-(L.sub.5).sub.a5-*' indicates a single bond; when a4 is 0,
*-(L.sub.4).sub.a4-*' indicates a single bond; when a5 is 0,
*-(L.sub.5).sub.a5-*' indicates a single bond; when a6 is 0,
*-(L.sub.6).sub.a6-*' indicates a single bond; when a7 is 0,
*-(L.sub.7).sub.a7-*' indicates a single bond; when a8 is 0,
*-(L.sub.8).sub.a8-*' indicates a single bond; when a9 is 0,
*-(L.sub.9).sub.a9-*' indicates a single bond; when a21 is 0,
*-(L.sub.21).sub.a21-*' indicates a single bond; and when a22 is 0,
*-(L.sub.22).sub.a22-*' indicates a single bond.
[0131] In one embodiment, a1 to a9, a21, and a22 in Formulae 1A to
1E and 2A to 2B may each independently be an integer selected from
0 to 3, but embodiments of the present disclosure are not limited
thereto.
[0132] In Formulae 1A to 1E, 2A, and 2B,
[0133] R.sub.1 to R.sub.9 may each independently be selected from
hydrogen, deuterium (-D), --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a substituted or unsubstituted C.sub.1-C.sub.60
alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60
alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60
alkynyl group, a substituted or unsubstituted C.sub.1-C.sub.60
alkoxy group, a substituted or unsubstituted C.sub.3-C.sub.10
cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkyl group, a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted
C.sub.1-C.sub.10 heterocycloalkenyl group, a substituted or
unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or
unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or
unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or
unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or
unsubstituted monovalent non-aromatic condensed polycyclic group,
--Si(Q.sub.1)(Q.sub.2)(Q.sub.3), --N(Q.sub.1)(Q.sub.2),
--B(Q.sub.1)(Q.sub.2), --C(.dbd.O)(Q.sub.1),
--S(.dbd.O).sub.2(Q.sub.1), and --P(.dbd.O)(Q.sub.1)(Q.sub.2),
[0134] R.sub.21 to R.sub.24 may each independently be selected from
hydrogen, deuterium (-D), --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a substituted or unsubstituted C.sub.1-C.sub.60
alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60
alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60
alkynyl group, a substituted or unsubstituted C.sub.1-C.sub.60
alkoxy group, a substituted or unsubstituted C.sub.3-C.sub.10
cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkyl group, a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted
C.sub.1-C.sub.10 heterocycloalkenyl group, a substituted or
unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or
unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or
unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or
unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or
unsubstituted monovalent non-aromatic condensed polycyclic group, a
substituted or unsubstituted monovalent non-aromatic condensed
heteropolycyclic group, --Si(Q.sub.4)(Q.sub.5)(Q.sub.6),
--N(Q.sub.4)(Q.sub.5), --B(Q.sub.4)(Q.sub.5), --C(.dbd.O)(Q.sub.4),
--S(.dbd.O).sub.2(Q.sub.4), and --P(.dbd.O)(Q.sub.4)(Q.sub.5).
Q.sub.1 to Q.sub.6 may each independently be the same as described
above.
[0135] For example, in Formulae 1A to 1E, 2A, and 2B,
[0136] R.sub.1 to R.sub.9 may each independently be selected from
the group consisting of:
[0137] hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group,
a cyano group, a nitro group, an amidino group, a hydrazino group,
a hydrazono group, a C.sub.1-C.sub.20 alkyl group, and a
C.sub.1-C.sub.20 alkoxy group;
[0138] a cyclopentyl group, a cyclohexyl group, a cycloheptyl
group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group,
a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl
group, a naphthyl group, an azulenyl group, a heptalenyl group, an
indacenyl group, an acenaphthyl group, a fluorenyl group, a
spiro-bifluorenyl group, a spiro-benzofluorene-fluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group,
a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group,
a triphenylenyl group, a pyrenyl group, a chrysenyl group, a
naphthacenyl group, a picenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl
group, a thiophenyl group, a furanyl group, a silolyl group, an
imidazolyl group, a pyrazolyl group, a thiazolyl group, an
isothiazolyl group, an oxazolyl group, an isoxazolyl group, a
pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a
pyridazinyl group, an indolyl group, an isoindolyl group, an
indazolyl group, a purinyl group, a quinolinyl group, an
isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group,
a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group,
a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group,
a benzofuranyl group, a benzothiophenyl group, a benzosilolyl
group, an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
oxadiazolyl group, a triazinyl group, a benzocarbazolyl group, a
dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl
group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a
thiazolopyridinyl group, a benzonaphthyridinyl group, an
azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl
group, an azadibenzofuranyl group, an azadibenzothiophenyl group,
an azadibenzosilolyl group, --Si(Q.sub.1)(Q.sub.2)(Q.sub.3),
--N(Q.sub.1)(Q.sub.2), --B(Q.sub.1)(Q.sub.2), --C(.dbd.O)(Q.sub.1),
--S(.dbd.O).sub.2(Q.sub.1), and --P(.dbd.O)(Q.sub.1)(Q.sub.2),
and
[0139] a cyclopentyl group, a cyclohexyl group, a cycloheptyl
group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group,
a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl
group, a naphthyl group, an azulenyl group, a heptalenyl group, an
indacenyl group, an acenaphthyl group, a fluorenyl group, a
spiro-bifluorenyl group, a spiro-benzofluorene-fluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group,
a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group,
a triphenylenyl group, a pyrenyl group, a chrysenyl group, a
naphthacenyl group, a picenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl
group, a thiophenyl group, a furanyl group, a silolyl group, an
imidazolyl group, a pyrazolyl group, a thiazolyl group, an
isothiazolyl group, an oxazolyl group, an isoxazolyl group, a
pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a
pyridazinyl group, an indolyl group, an isoindolyl group, an
indazolyl group, a purinyl group, a quinolinyl group, an
isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group,
a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group,
a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group,
a benzofuranyl group, a benzothiophenyl group, a benzosilolyl
group, an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
oxadiazolyl group, a triazinyl group, a benzocarbazolyl group, a
dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl
group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a
thiazolopyridinyl group, a benzonaphthyridinyl group, an
azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl
group, an azadibenzofuranyl group, an azadibenzothiophenyl group,
and an azadibenzosilolyl group, each substituted with at least one
selected from deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a
C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10
cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a
C.sub.6-C.sub.60 aryl group, a C.sub.1-C.sub.60 heteroaryl group, a
monovalent non-aromatic condensed polycyclic group, a monovalent
non-aromatic condensed heteropolycyclic group, a biphenyl group, a
terphenyl group, --Si(Q.sub.31)(Q.sub.32)(Q.sub.33),
--N(Q.sub.31)(Q.sub.32), --B(Q.sub.31)(Q.sub.32),
--C(.dbd.O)(Q.sub.31), --S(.dbd.O).sub.2(Q.sub.31), and
--P(.dbd.O)(Q.sub.31)(Q.sub.32),
[0140] R.sub.21 to R.sub.24, R.sub.27, and R.sub.28 may each
independently be selected from the group consisting of:
[0141] hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group,
a cyano group, a nitro group, an amidino group, a hydrazino group,
a hydrazono group, a C.sub.1-C.sub.20 alkyl group, and a
C.sub.1-C.sub.20 alkoxy group;
[0142] a cyclopentyl group, a cyclohexyl group, a cycloheptyl
group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group,
a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl
group, a naphthyl group, an azulenyl group, a heptalenyl group, an
indacenyl group, an acenaphthyl group, a fluorenyl group, a
spiro-bifluorenyl group, a spiro-benzofluorene-fluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group,
a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group,
a triphenylenyl group, a pyrenyl group, a chrysenyl group, a
naphthacenyl group, a picenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl
group, a thiophenyl group, a furanyl group, a silolyl group, an
imidazolyl group, a pyrazolyl group, a thiazolyl group, an
isothiazolyl group, and oxazolyl group, an isoxazolyl group, a
pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a
pyridazinyl group, an indolyl group, an isoindolyl group, an
indazolyl group, a purinyl group, a quinolinyl group, an
isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group,
a napthyridinyl group, a quinoxalinyl group, a quinazolinyl group,
a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group,
a benzofuranyl group, a benzothiophenyl group, a benzosilolyl
group, an isobenzothiazolyl group, a benzoxazoyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
oxadiazolyl group, a trianzinyl group, a dibenzofuranyl group, a
dibenzothiophenyl group, a dibenzosilolyl group, a carbazolyl
group, a benzocarbazolyl group, a dibenzocarbazolyl group, a
thiadiazolyl group, an imidazopyridinyl group, an
imidazopyrimidinyl group, and oxazolopyridinyl group, a
thiazolopyridinyl group, a benzonaphthyridinyl group, an
azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl
group, an azadibenzofuranyl group, an azadibenzothiophenyl group,
an azadibenzosilolyl group, --Si(Q.sub.4)(Q.sub.5)(Q.sub.6),
--N(Q.sub.4)(Q.sub.5), --B(Q.sub.4)(Q.sub.5), --C(.dbd.O)(Q.sub.4),
--S(.dbd.O).sub.2(Q.sub.4), and --P(.dbd.O)(Q.sub.4)(Q.sub.5);
and
[0143] a cyclopentyl group, a cyclohexyl group, a cycloheptyl
group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group,
a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl
group, a naphthyl group, an azulenyl group, a heptalenyl group, an
indacenyl group, an acenaphthyl group, a fluorenyl group, a
spiro-bifluorenyl group, a spiro-benzofluorene-fluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group,
a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group,
a triphenylenyl group, a pyrenyl group, a chrysenyl group, a
naphthacenyl group, a picenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacentyl group, a
rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl
group, a thiophenyl group, a furanyl group, a silolyl group, an
imidazolyl group, a pyrazolyl group, a thiazolyl group, an
isothiazolyl group, an oxazolyl group, an isoxazolyl group, a
pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a
pyridazinyl group, an indolyl group, an isoindolyl group, an
indazolyl group, a purinyl group, a quinolinyl group, an
isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group,
a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group,
a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group,
a benzofuranyl group, a benzothiophenyl group, a benzosilolyl
group, an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a
dibenzothiophenyl group, a dibenzosilolyl group, a carbazolyl
group, a benzocarbazolyl group, a dibenzocarbazolyl group, a
thiadiazolyl group, an imidazopyridinyl group, an
imidazopyrimidinyl group, an oxazolopyridinyl group, a
thiazolopyridinyl group, a benzonaphthyridinyl group, an
azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl
group, an azadibenzofuranyl group, an azadibenzothiophenyl group,
and an azadibenzosilolyl group, each substituted with at least one
selected from deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a
C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10
cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a
C.sub.6-C.sub.60 aryl group, a C.sub.1-C.sub.60 heteroaryl group, a
monovalent non-aromatic condensed polycyclic group, a monovalent
non-aromatic condensed heteropolycyclic group, a biphenyl group, a
terphenyl group, --Si(Q.sub.31)(Q.sub.32)(Q.sub.33),
--N(Q.sub.31)(Q.sub.32), --B(Q.sub.31)(Q.sub.32),
--C(.dbd.O)(Q.sub.31), --S(.dbd.O).sub.2(Q.sub.31), and
--P(.dbd.O)(Q.sub.31)(Q.sub.32),
[0144] wherein Q.sub.1 to Q.sub.6 and Q.sub.31 to Q.sub.33 may each
independently be selected from the group consisting of:
[0145] a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy
group, a phenyl group, a biphenyl group, a terphenyl group, a
naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl
group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl
group, and a quinazolinyl group; and
[0146] a phenyl group, a biphenyl group, a terphenyl group, a
naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl
group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl
group, and a quinazolinyl group, each substituted with at least one
selected from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10
alkoxy group, and a phenyl group.
[0147] For example, in Formulae 1A to 1E, 2A, and 2B,
[0148] R.sub.1 to R.sub.9 may each independently be selected from
the group consisting of:
[0149] hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group,
a cyano group, a nitro group, an amidino group, a hydrazino group,
a hydrazono group, a C.sub.1-C.sub.20 alkyl group, and a
C.sub.1-C.sub.20 alkoxy group;
[0150] a phenyl group, a biphenyl group, a terphenyl group, a
pentalenyl group, an indenyl group, a naphthyl group, an azulenyl
group, a heptalenyl group, an indacenyl group, an acenaphthyl
group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a
spiro-benzofluorene-fluorenyl group, an indenofluorenyl group, a
phenalenyl group, a phenanthrenyl group, an anthracenyl group, a
fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a
chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl
group, a pentaphenyl group, a hexacenyl group, a pentacenyl group,
a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl
group, a thiophenyl group, a furanyl group, an imidazolyl group, a
pyrazolyl group, a thiazolyl group, an isothiazolyl group, an
oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl
group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl
group, an indolyl group, an indazolyl group, a purinyl group, a
quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group,
a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group,
a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group,
an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a
benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl
group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl
group, an oxadiazolyl group, a triazinyl group, a thiadiazolyl
group, an imidazopyridinyl group, an imidazopyrimidinyl group,
--Si(Q.sub.1)(Q.sub.2)(Q.sub.3), --N(Q.sub.1)(Q.sub.2),
--B(Q.sub.1)(Q.sub.2), --C(.dbd.O)(Q.sub.1),
--S(.dbd.O).sub.2(Q.sub.1), and --P(.dbd.O)(Q.sub.1)(Q.sub.2),
and
[0151] a phenyl group, a biphenyl group, a terphenyl group, a
pentalenyl group, an indenyl group, a naphthyl group, an azulenyl
group, a heptalenyl group, an indacenyl group, an acenaphthyl
group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a
spiro-benzofluorene-fluorenyl group, an indenofluorenyl group, a
phenalenyl group, a phenanthrenyl group, an anthracenyl group, a
fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a
chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl
group, a pentaphenyl group, a hexacenyl group, a pentacenyl group,
a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl
group, a thiophenyl group, a furanyl group, an imidazolyl group, a
pyrazolyl group, a thiazolyl group, an isothiazolyl group, an
oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl
group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl
group, an indolyl group, an indazolyl group, a purinyl group, a
quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group,
a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group,
a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group,
an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a
benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl
group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl
group, an oxadiazolyl group, a triazinyl group, a thiadiazolyl
group, an imidazopyridinyl group, and an imidazopyrimidinyl group,
each substituted with at least one selected from deuterium, --F,
--Cl, --Br, --I, a hydroxyl group, a cyano group, a nitro group, an
amidino group, a hydrazino group, a hydrazono group, a
C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a
C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, a monovalent non-aromatic
condensed heteropolycyclic group, a biphenyl group, a terphenyl
group, --Si(Q.sub.31)(Q.sub.32)(Q.sub.33), --N(Q.sub.31)(Q.sub.32),
--B(Q.sub.31)(Q.sub.32), --C(.dbd.O)(Q.sub.31),
--S(.dbd.O).sub.2(Q.sub.31), and
--P(.dbd.O)(Q.sub.31)(Q.sub.32),
[0152] R.sub.21 to R.sub.24, R.sub.27, and R.sub.28 may each
independently be selected from the group consisting of:
[0153] a phenyl group, a biphenyl group, a terphenyl group, a
pentalenyl group, an indenyl group, a naphthyl group, an azulenyl
group, an indacenyl group, an acenaphthyl group, a fluorenyl group,
a spiro-bifluorenyl group, a benzofluorenyl group, a
dibenzofluorenyl group, a spiro-benzofluorene-fluorenyl group, an
indenofluorenyl group, a phenalenyl group, a phenanthrenyl group,
an anthracenyl group, a fluoranthenyl group, a triphenylenyl group,
a pyrenyl group, a chrysenyl group, a picenyl group, a perylenyl
group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, a
thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl
group, a thiazolyl group, an isothiazolyl group, an oxazolyl group,
an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a
pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an
indolyl group, an indazolyl group, a purinyl group, a quinolinyl
group, an isoquinolinyl group, a benzoquinolinyl group, a
phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a
quinazolinyl group, a cinnolinyl group, a carbazolyl group, a
phenanthridinyl group, an acridinyl group, a phenanthrolinyl group,
a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a
benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl
group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl
group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl
group, a dibenzothiophenyl group, a benzocarbazolyl group, a
dibenzocarbazolyl group, a dibenzosilolyl group, a thiadiazolyl
group, an imidazopyridinyl group, an imidazopyrimidinyl group,
--Si(Q.sub.4)(Q.sub.5)(Q.sub.6), --N(Q.sub.4)(Q.sub.5),
--B(Q.sub.4)(Q.sub.6), --C(.dbd.O)(Q.sub.4),
--S(.dbd.O).sub.2(Q.sub.4), and --P(.dbd.O)(Q.sub.4)(Q.sub.5);
and
[0154] a phenyl group, a biphenyl group, a terphenyl group, a
pentalenyl group, an indenyl group, a naphthyl group, an azulenyl
group, an indacenyl group, an acenaphthyl group, a fluorenyl group,
a spiro-bifluorenyl group, a benzofluorenyl group, a
dibenzofluorenyl group, a spiro-benzofluorene-fluorenyl group, an
indenofluorenyl group, a phenalenyl group, a phenanthrenyl group,
an anthracenyl group, a fluoranthenyl group, a triphenylenyl group,
a pyrenyl group, a chrysenyl group, a picenyl group, a perylenyl
group, a pentaphenyl group, a pentacenyl group, a pyrrolyl group, a
thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl
group, a thiazolyl group, an isothiazolyl group, an oxazolyl group,
an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a
pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an
indolyl group, an indazolyl group, a purinyl group, a quinolinyl
group, an isoquinolinyl group, a benzoquinolinyl group, a
phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a
quinazolinyl group, a cinnolinyl group, a carbazolyl group, a
phenanthridinyl group, an acridinyl group, a phenanthrolinyl group,
a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a
benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl
group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl
group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl
group, a dibenzothiophenyl group, a benzocarbazolyl group, a
dibenzocarbazolyl group, a dibenzosilolyl group, a thiadiazolyl
group, an imidazopyridinyl group, and an imidazopyrimidinyl group,
each substituted with at least one selected from deuterium, --F,
--Cl, --Br, --I, a hydroxyl group, a cyano group, a nitro group, an
amidino group, a hydrazino group, a hydrazono group, a
C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a
C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, a monovalent non-aromatic
condensed heteropolycyclic group, a biphenyl group, a terphenyl
group, --Si(Q.sub.31)(Q.sub.32)(Q.sub.33), --N(Q.sub.31)(Q.sub.32),
--B(Q.sub.31)(Q.sub.32), --C(.dbd.O)(Q.sub.31),
--S(.dbd.O).sub.2(Q.sub.31), and
--P(.dbd.O)(Q.sub.31)(Q.sub.32),
[0155] R.sub.22 to R.sub.24, R.sub.27, and R.sub.28 may each
independently be selected from hydrogen, deuterium, --F, --Cl,
--Br, --I, a hydroxyl group, a cyano group, a nitro group, an
amidino group, a hydrazino group, a hydrazono group, a
C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group,
--Si(Q.sub.4)(Q.sub.5)(Q.sub.6), --S(.dbd.O).sub.2(Q.sub.4), and
--P(.dbd.O)(Q.sub.4)(Q.sub.5), and
[0156] Q.sub.1 to Q.sub.6 and Q.sub.31 to Q.sub.33 may each
independently be selected from the group consisting of:
[0157] a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy
group, a phenyl group, a biphenyl group, a terphenyl group, a
naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl
group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl
group, and a quinazolinyl group; and
[0158] a phenyl group, a biphenyl group, a terphenyl group, a
naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl
group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl
group, and a quinazolinyl group, each substituted with at least one
selected from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10
alkoxy group, and a phenyl group.
[0159] In one or more embodiments, in Formulae 1A to 1E, 2A, and
2B,
[0160] R.sub.1 to R.sub.9 may each independently be selected from
the group consisting of:
[0161] hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group,
a cyano group, a nitro group, an amidino group, a hydrazino group,
a hydrazono group, a C.sub.1-C.sub.20 alkyl group, and a
C.sub.1-C.sub.20 alkoxy group;
[0162] a group represented by any of Formulae 5-1 to 5-44, 6-1 to
6-121, 6-123, and 6-124; and
[0163] --Si(Q.sub.1)(Q.sub.2)(Q.sub.3), --N(Q.sub.1)(Q.sub.2),
--B(Q.sub.1)(Q.sub.2), --C(.dbd.O)(Q.sub.1),
--S(.dbd.O).sub.2(Q.sub.1), and --P(.dbd.O)(Q.sub.1)(Q.sub.2),
[0164] when R.sub.1 to R.sub.9 are selected from groups represented
by Formulae 5-13 to 5-36 and 5-43, Y.sub.31 and Y.sub.32 in
Formulae 5-13 to 5-36 and 5-43 may each independently be
C(Z.sub.33)(Z.sub.34),
[0165] R.sub.21 may be selected from groups represented by Formulae
5-1 to 5-45 and 6-1 to 6-124,
[0166] R.sub.22 to R.sub.24, R.sub.27, and R.sub.28 may each
independently be selected from the group consisting of:
[0167] hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group,
a cyano group, a nitro group, an amidino group, a hydrazino group,
a hydrazono group, a C.sub.1-C.sub.20 alkyl group, and a
C.sub.1-C.sub.20 alkoxy group;
[0168] a group represented by any of Formulae 5-1 to 5-45 and
Formulae 6-1 to 6-124; and
[0169] --Si(Q.sub.4)(Q.sub.5)(Q.sub.6), --N(Q.sub.4)(Q.sub.5),
--B(Q.sub.4)(Q.sub.5), --C(.dbd.O)(Q.sub.4),
--S(.dbd.O).sub.2(Q.sub.4), and --P(.dbd.O)(Q.sub.4)(Q.sub.5), but
embodiments of the present disclosure are not limited thereto:
##STR00045## ##STR00046## ##STR00047## ##STR00048## ##STR00049##
##STR00050## ##STR00051## ##STR00052## ##STR00053## ##STR00054##
##STR00055## ##STR00056## ##STR00057## ##STR00058## ##STR00059##
##STR00060## ##STR00061## ##STR00062## ##STR00063## ##STR00064##
##STR00065## ##STR00066## ##STR00067## ##STR00068##
[0170] In Formulae 5-1 to 5-45 and 6-1 to 6-124,
[0171] Y.sub.31 and Y.sub.32 may each independently be O, S,
C(Z.sub.33)(Z.sub.34), N(Z.sub.35), or Si(Z.sub.36)(Z.sub.37),
[0172] Y.sub.41 may be N or C(Z.sub.41), Y.sub.42 may be N or
C(Z.sub.42), Y.sub.43 may be N or C(Z.sub.43), Y.sub.44 may be N or
C(Z.sub.44), Y.sub.51 may be N or C(Z.sub.51), Y.sub.52 may be N or
C(Z.sub.52), Y.sub.53 may be N or C(Z.sub.53), Y.sub.54 may be N or
C(Z.sub.54), at least one selected from Y.sub.41 to Y.sub.43 and
Y.sub.51 to Y.sub.54 in Formulae 5-118 to 5-121 may be N, and at
least one selected from Y.sub.41 to Y.sub.44 and Y.sub.51 to
Y.sub.54 in Formula 5-122 may be N,
[0173] Z.sub.31 to Z.sub.37, Z.sub.41 to Z.sub.44, and Z.sub.51 to
Z.sub.54 may each independently be selected from hydrogen,
deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a cyano group, a
nitro group, an amidino group, a hydrazino group, a hydrazono
group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy
group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl
group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group,
a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl
group, a naphthyl group, an azulenyl group, a heptalenyl group, an
indacenyl group, an acenaphthyl group, a fluorenyl group, a
spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl
group, a phenalenyl group, a phenanthrenyl group, an anthracenyl
group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl
group, a chrysenyl group, a naphthacenyl group, a picenyl group, a
perylenyl group, a pentaphenyl group, a hexacenyl group a
pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl
group, a pyrrolyl group, a thiophenyl group, a furanyl group, a
silolyl group, and imidazolyl group, a pyrazolyl group, a thiazolyl
group, an isothiazolyl group, an oxazolyl group, an isoxazolyl
group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a
pyridazinyl group, an indolyl group, an isoindolyl group, an
indazolyl group, a purinyl group, a quinolinyl group, an
isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group,
a naphthyridinyl group, a quinozalinyl group, a quinazolinyl group,
a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group,
a benzofuranyl group, a benzothiophenyl group, a benzosilolyl
group, an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a
dibenzothiophenyl group, a dibenzosilolyl group, a carbazolyl
group, a benzocarbazolyl group, a dibenzocarbazolyl group, a
thiadiazolyl group, an imidazopyridinyl group, an
imidazopyrimidinyl group, a benzoaphthyridinyl group, an
azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl
group, an azadibenzofuranyl group, an azadibenzothiophenyl group,
an azadibenzosilolyl group, and
--Si(Q.sub.31)(Q.sub.32)(Q.sub.33),
[0174] Q.sub.1 to Q.sub.3 and Q.sub.31 to Q.sub.33 may each
independently be selected from the group consisting of:
[0175] a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy
group, a phenyl group, a biphenyl group, a terphenyl group, a
naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl
group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl
group, and a quinazolunyl group; and
[0176] a phenyl group, a biphenyl group, a terphenyl group, a
paphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl
group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl
group, and a quinazolinyl group, each substituted with at least one
selected from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10
alkoxy group, and a phenyl group,
[0177] e3 may be an integer selected from 0 to 3,
[0178] e2 may be an integer selected from 0 to 2,
[0179] e4 may be an integer selected from 0 to 4,
[0180] e5 may be an integer selected from 0 to 5,
[0181] e6 may be an integer selected from 0 to 6,
[0182] e7 may be an integer selected from 0 to 7,
[0183] e9 may be an integer selected from 0 to 9, and
[0184] * may indicate a binding site to a neighboring atom.
[0185] In one or more embodiments,
[0186] in Formulae 1A to 1E, 2A, and 2B,
[0187] R.sub.1 to R.sub.9 may each independently be selected from
the group consisting of:
[0188] hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group,
a cyano group, a nitro group, an amidino group, a hydrazino group,
a hydrazono group, a C.sub.1-C.sub.20 alkyl group, and a
C.sub.1-C.sub.20 alkoxy group;
[0189] a group represented by any of Formulae 9-1 to 9-28, 9-53 to
9-88, and 10-1 to 10-121; and
[0190] --Si(Q.sub.1)(Q.sub.2)(Q.sub.3), --N(Q.sub.1)(Q.sub.2),
--B(Q.sub.1)(Q.sub.2), --C(.dbd.O)(Q.sub.1),
--S(.dbd.O).sub.2(Q.sub.1), and --P(.dbd.O)(Q.sub.1)(Q.sub.2),
[0191] R.sub.21 may be selected from groups represented by Formulae
9-1 to 9-100 and 10-1 to 10-121,
[0192] R.sub.22 to R.sub.24 may each independently be selected from
the group consisting of:
[0193] hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group,
a cyano group, a nitro group, an amidino group, a hydrazino group,
a hydrazono group, a C.sub.1-C.sub.20 alkyl group, and a
C.sub.1-C.sub.20 alkoxy group;
[0194] a group represented by any of Formulae 9-1 to 9-100 and 10-1
to 10-121; and
[0195] --Si(Q.sub.4)(Q.sub.5)(Q.sub.6), --N(Q.sub.4)(Q.sub.5),
--B(Q.sub.4)(Q.sub.5), --C(.dbd.O)(Q.sub.4),
--S(.dbd.O).sub.2(Q.sub.4), and --P(.dbd.O)(Q.sub.4)(Q.sub.5), but
embodiments of the present disclosure are not limited thereto:
##STR00069## ##STR00070## ##STR00071## ##STR00072## ##STR00073##
##STR00074## ##STR00075## ##STR00076## ##STR00077## ##STR00078##
##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083##
##STR00084## ##STR00085## ##STR00086## ##STR00087## ##STR00088##
##STR00089## ##STR00090## ##STR00091## ##STR00092## ##STR00093##
##STR00094## ##STR00095## ##STR00096## ##STR00097## ##STR00098##
##STR00099## ##STR00100## ##STR00101## ##STR00102##
##STR00103##
[0196] In Formulae 9-1 to 9-100 and 10-1 to 10-121, Ph indicates a
phenyl group, and * indicates a binding site to a neighboring
atom.
[0197] b1 to b7, b21, and b22 in Formulae 1A to 1E, 2A, and 2B
indicate the numbers of R.sub.1 to R.sub.9, R.sub.21, and R.sub.22
groups, respectively. b1 to b7, b21, and b22 may each independently
be an integer selected from 1 to 3. When b1 is two or more, two or
more R.sub.1(s) may be identical to or different from each other;
when b2 is two or more, two or more R.sub.2(s) may be identical to
or different from each other; when b3 is two or more, two or more
R.sub.3(s) may be identical to or different from each other; when
b4 is two or more, two or more R.sub.4(s) may be identical to or
different from each other; when b5 is two or more, two or more
R.sub.5(s) may be identical to or different from each other; when
b6 is two or more, two or more R.sub.6(s) may be identical to or
different from each other; when b7 is two or more, two or more
R.sub.7(s) may be identical to or different from each other; when
b8 is two or more, two or more R.sub.5(s) may be identical to or
different from each other; when b9 is two or more, two or more
R.sub.9(s) may be identical to or different from each other; when
b21 is two or more, two or more R.sub.21(s) may be identical to or
different from each other; and when b22 is two or more, two or more
R.sub.22(s) may be identical to or different from each other.
[0198] In one embodiment, b1 to b9, b21, and b22 in Formulae 1A to
1E, 2A, and 2B may each independently be 1 or 2, but embodiments of
the present disclosure are not limited thereto.
[0199] c1, c2, and c5 to c9 in Formulae 1A to 1E indicate the
number of *-[(L.sub.1).sub.a1-(R.sub.1).sub.b1],
*-[(L.sub.2).sub.a2-(R.sub.2).sub.b2],
*-[(L.sub.5).sub.a5-(R.sub.5).sub.b5],
*-[(L.sub.6).sub.a6-(R.sub.6).sub.bd],
*-[(L.sub.7).sub.a7-(R.sub.7).sub.b7],
*-[(L.sub.8).sub.a8-(R.sub.8).sub.b8], and
*-[(L.sub.9).sub.a9-(R.sub.9).sub.b9] groups, respectively. c1, c2,
and c5 to c7 in Formulae 1A to 1E may each independently be an
integer selected from 0 to 10, provided that the sum of c5, c6, and
c7 is 1 or more, and c8 and c9 may each independently be an integer
selected from 0 to 4, provided that the sum of c8 and c9 is 1 or
more.
[0200] In Formulae 1A to 1E, when c1 is two or more, two or more
*-[(L.sub.1).sub.a1-(R.sub.1).sub.b1](s) may be identical to or
different from each other; when c2 is two or more, two or more
*-[(L.sub.2).sub.a2-(R.sub.2).sub.b2](s) may be identical to or
different from each other; when c5 is two or more, two or more
*-[(L.sub.5).sub.a5-(R.sub.5).sub.b5](s) may be identical to or
different from each other; when c6 is two or more, two or more
*-[(L.sub.6).sub.a6-(R.sub.6).sub.b6](s) may be identical to or
different from each other; when c7 is two or more, two or more
*-[(L.sub.7).sub.a7-(R.sub.7).sub.b7](s) may be identical to or
different from each other; when c8 is two or more, two or more
*-[(L.sub.8).sub.a8-(R.sub.8).sub.b8](s) may be identical to or
different from each other; and when c9 is two or more, two or more
*-[(L.sub.9).sub.a9-(R.sub.9).sub.b9](s) may be identical to or
different from each other.
[0201] In one embodiment, c1, c2, and c5 to c7 in Formulae 1A to 1E
may each independently be an integer selected from 0 to 8, provided
that the sum of c5, c6, and c7 is 1 or more.
[0202] In one embodiment, the first compound represented by one
selected from Formulae 1A to 1E may be represented by one selected
from Formula 1E and Formulae 1-1 to 1-6:
##STR00104##
[0203] Formula 1E may be the same as described above,
[0204] in Formulae 1-1 to 1-6, rings A.sub.11 to A.sub.13, L.sub.1
to L.sub.6, a1 to a6, R.sub.1 to R.sub.6, and b1 to b6 may each
independently be the same as described herein in connection with
Formulae 1A to 1D,
[0205] c1, c2, and c6 may each independently be an integer selected
from 0 to 10, and
[0206] c5 may be an integer selected from 1 to 10.
[0207] In one or more embodiments, the first compound represented
by one selected from Formulae 1A to 1E may be represented by one
selected from Formulae 1(1) to 1(11), but embodiments of the
present disclosure are not limited thereto:
##STR00105## ##STR00106##
[0208] In Formulae 1(1) to 1(11),
[0209] L.sub.1 to L.sub.9, a1 to a9, R.sub.1 to R.sub.9, and b1 to
b9 may each independently be the same as described above,
[0210] R.sub.2a to R.sub.2h may each independently be the same as
described herein in connection with R.sub.2,
[0211] R.sub.8a to R.sub.8c may each be the same as described in
connection with R.sub.8,
[0212] R.sub.9a to R.sub.9c may each be the same as described in
connection with R.sub.9,
[0213] c1a may be an integer selected from 0 to 4,
[0214] c2a may be an integer selected from 0 to 4,
[0215] c2b may be an integer selected from 0 to 6,
[0216] c5a may be an integer selected from 0 to 4,
[0217] c5b may be an integer selected from 0 to 3,
[0218] c6a may be an integer selected from 0 to 4, and
[0219] the sum of c5a and c6a or the sum of c5b and c6a may be 1 or
more.
[0220] In one embodiment, the first compound represented by one
selected from Formulae 1A to 1E may be selected from Compounds 1-1
to 1-93:
##STR00107## ##STR00108## ##STR00109## ##STR00110## ##STR00111##
##STR00112## ##STR00113## ##STR00114## ##STR00115## ##STR00116##
##STR00117## ##STR00118## ##STR00119##
[0221] In one or more embodiments, the second compound represented
by Formula 2A or 2B may be selected from Compounds 2-1a to 2-172a
and 2-1 to 2-262, but embodiments of the present disclosure are not
limited thereto:
##STR00120## ##STR00121## ##STR00122## ##STR00123## ##STR00124##
##STR00125## ##STR00126## ##STR00127## ##STR00128## ##STR00129##
##STR00130## ##STR00131## ##STR00132## ##STR00133## ##STR00134##
##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139##
##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144##
##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149##
##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154##
##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159##
##STR00160## ##STR00161## ##STR00162## ##STR00163## ##STR00164##
##STR00165## ##STR00166## ##STR00167## ##STR00168## ##STR00169##
##STR00170## ##STR00171## ##STR00172## ##STR00173## ##STR00174##
##STR00175## ##STR00176## ##STR00177## ##STR00178## ##STR00179##
##STR00180## ##STR00181## ##STR00182## ##STR00183## ##STR00184##
##STR00185## ##STR00186## ##STR00187## ##STR00188## ##STR00189##
##STR00190## ##STR00191## ##STR00192##
[0222] In Formulae 1A to 1E, any suitable combination of ring
A.sub.11, ring A.sub.12, ring A.sub.13, X.sub.11, X.sub.12, L.sub.1
to L.sub.9, a1 to a9, R.sub.1 to R.sub.9, b1 to b9, and c1 to c9
may be used within the scope described herein.
[0223] In Formulae 2A and 2B, any suitable combination of ring
A.sub.21, ring A.sub.22, ring A.sub.23, X.sub.21, and T.sub.11 to
T.sub.14 may be used within the scope described herein. Regarding
*-[(L.sub.22).sub.a22-(R.sub.22).sub.b22], C(R.sub.23)(R.sub.24),
Si(R.sub.23)(R.sub.24), and
N-[(L.sub.21).sub.a21-(R.sub.21).sub.b21], any suitable combination
of L.sub.21, L.sub.22, a21, a22, R.sub.21 to R.sub.24, b21, and b22
may be used within the scope described herein.
[0224] In the organic light-emitting device, the emission layer may
include the first compound, and at least one selected from the hole
transport region and the electron transport region may include the
second compound represented by Formula 2A or 2B. Accordingly,
electrons and/or holes injected into or transported to the emission
layer may be easily balanced to prevent current leakage, thereby
enabling low driving voltage and high efficiency
characteristics.
[0225] In one embodiment, the second compound represented by
Formula 2A or 2B may have a triplet energy of 2.2 eV or more, for
example, 2.3 eV or more, and in some embodiments, 2.4 eV or
more.
[0226] When the second compound represented by Formula 2A or 2B
satisfies these triplet energy ranges, for example, the luminescent
efficiency of a fluorescent organic light-emitting device may be
improved due to triplet-triplet fusion (TTF), or triplet excitons
formed in the emission layer of a phosphorescent organic
light-emitting device may not be transitioned (e.g., the
probability of triplet exciton loss may be reduced), thereby
preventing or reducing a decrease in efficiency of an organic
light-emitting device.
[0227] In one embodiment, the emission layer may include the first
compound represented by one selected from Formulae 1A to 1E as a
first host.
[0228] In one embodiment, the emission layer may further include,
in addition to the first host, a second host that is different from
the first host.
[0229] In one embodiment, the hole transport region may include an
emission auxiliary layer, the emission auxiliary layer may directly
contact the emission layer, and the emission auxiliary layer may
include the second compound represented by Formula 2A or 2B.
[0230] In one or more embodiments, the electron transport region
may include a buffer layer, the buffer layer may directly contact
the emission layer, and the buffer layer may include the second
compound represented by Formula 2A or 2B, but embodiments of the
hole transport region and the electron transport region are not
limited thereto.
[0231] When each of the hole transport region and the electron
transport region in the organic light-emitting device includes the
second compound represented by Formula 2A or 2B, the second
compound included in the hole transport region may be identical to
or different from the second compound included in the electron
transport region.
[0232] The emission layer may include a dopant, and the dopant may
be an organometallic complex.
Description of FIG. 1
[0233] FIG. 1 is a schematic view of an organic light-emitting
device 10 according to an embodiment of the present disclosure. The
organic light-emitting device 10 includes a first electrode 110, an
organic layer 150, and a second electrode 190.
[0234] Hereinafter, the structure of the organic light-emitting
device 10 according to an embodiment of the present disclosure and
a method of manufacturing the organic light-emitting device 10 will
be described in connection with FIG. 1.
First Electrode 110
[0235] In FIG. 1, a substrate may be under the first electrode 110
or above the second electrode 190. The substrate may be a glass
substrate or a plastic substrate, each having excellent mechanical
strength, thermal stability, transparency, surface smoothness, ease
of handling, and/or water-resistance.
[0236] The first electrode 110 may be formed by depositing and/or
sputtering a material for forming the first electrode 110 on the
substrate. When the first electrode 110 is an anode, the material
for forming the first electrode 110 may be selected from materials
with a high work function in order to facilitate hole
injection.
[0237] The first electrode 110 may be a reflective electrode, a
semi-transmissive electrode, or a transmissive electrode. When the
first electrode 110 is a transmissive electrode, the material for
forming the first electrode may be selected from indium tin oxide
(ITO), indium zinc oxide (IZO), tin oxide (SnO.sub.2), zinc oxide
(ZnO), and combinations thereof, but embodiments of the present
disclosure are not limited thereto. When the first electrode 110 is
a semi-transmissive electrode or a reflective electrode, the
material for forming the first electrode 110 may be selected from
magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium
(Al--Li), calcium (Ca), magnesium-indium (Mg--In), magnesium-silver
(Mg--Ag), and combinations thereof. However, embodiments of the
material for forming the first electrode 110 are not limited
thereto.
[0238] The first electrode 110 may have a single-layer structure,
or a multi-layer structure including two or more layers. For
example, the first electrode 110 may have a three-layered structure
of ITO/Ag/ITO, but embodiments of the structure of the first
electrode 110 are not limited thereto.
Organic Layer 150
[0239] The organic layer 150 is on the first electrode 110. The
organic layer 150 may include an emission layer.
[0240] The organic layer 150 may include a hole transport region
between the first electrode 110 and the emission layer, and an
electron transport region between the emission layer and the second
electrode 190.
Hole Transport Region in Organic Layer 150
[0241] The hole transport region may have i) a single-layered
structure including a single layer including a single material, ii)
a single-layered structure including a single layer including a
plurality of different materials, or iii) a multi-layered structure
having a plurality of layers including a plurality of different
materials.
[0242] The hole transport region may include at least one layer
selected from a hole injection layer, a hole transport layer, an
emission auxiliary layer, and an electron blocking layer.
[0243] For example, the hole transport region may have a
single-layer structure including a single layer including a
plurality of different materials, or a multi-layer structure having
a structure of hole injection layer/hole transport layer, hole
injection layer/hole transport layer/emission auxiliary layer, hole
injection layer/emission auxiliary layer, hole transport
layer/emission auxiliary layer, or hole injection layer/hole
transport layer/electron blocking layer, wherein layers of each
structure are sequentially stacked on the first electrode 110 in
each stated order, but embodiments of the structure of the hole
transport region are not limited thereto.
[0244] The hole transport region may include the second compound
represented by Formula 2A or 2B as described above.
[0245] In one embodiment, the hole transport region may include an
emission auxiliary layer. The emission auxiliary layer may directly
contact the emission layer.
[0246] In one or more embodiments, the hole transport region may
include a hole injection layer and a hole transport layer stacked
in this stated order on the first electrode 110, a hole injection
layer and an emission auxiliary layer stacked in this stated order
on the first electrode 110, or a hole injection layer, a hole
transport layer, and an emission auxiliary layer, stacked in this
stated order on the first electrode 110, but embodiments of the
present disclosure are not limited thereto.
[0247] When the hole transport region includes an emission
auxiliary layer, the emission auxiliary layer may further include
the second compound represented by Formula 2A or 2B.
[0248] The hole transport region may include at least one selected
from m-MTDATA, TDATA, 2-TNATA, NPB(NPD), .beta.-NPB, TPD,
Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD,
4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA),
polyaniline/dodecylbenzenesulfonic acid (PAN I/DBSA),
poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate)
(PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA),
polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound
represented by Formula 201, and a compound represented by Formula
202:
##STR00193## ##STR00194## ##STR00195## ##STR00196##
[0249] In Formulae 201 and 202,
[0250] L.sub.201 to L.sub.204 may each independently be selected
from a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkylene
group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkylene group, a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkenylene group, a substituted or
unsubstituted C.sub.1-C.sub.10 heterocycloalkenylene group, a
substituted or unsubstituted C.sub.6-C.sub.60 arylene group, a
substituted or unsubstituted C.sub.1-C.sub.60 heteroarylene group,
a substituted or unsubstituted divalent non-aromatic condensed
polycyclic group, and a substituted or unsubstituted divalent
non-aromatic condensed heteropolycyclic group,
[0251] L.sub.205 may be selected from *--O--*', *--S--*',
*--N(Q.sub.201)-*', a substituted or unsubstituted C.sub.1-C.sub.20
alkylene group, a substituted or unsubstituted C.sub.2-C.sub.20
alkenylene group, a substituted or unsubstituted C.sub.3-C.sub.10
cycloalkylene group, a substituted or unsubstituted
C.sub.1-C.sub.10 heterocycloalkylene group, a substituted or
unsubstituted C.sub.3-C.sub.10 cycloalkenylene group, a substituted
or unsubstituted C.sub.1-C.sub.10 heterocycloalkenylene group, a
substituted or unsubstituted C.sub.6-C.sub.60 arylene group, a
substituted or unsubstituted C.sub.1-C.sub.60 heteroarylene group,
a substituted or unsubstituted divalent non-aromatic condensed
polycyclic group, and a substituted or unsubstituted divalent
non-aromatic condensed heteropolycyclic group,
[0252] xa1 to xa4 may each independently be an integer selected
from 0 to 3,
[0253] xa5 may be an integer selected from 1 to 10, and
[0254] R.sub.201 to R.sub.204 and Q.sub.201 may each independently
be selected from a substituted or unsubstituted C.sub.3-C.sub.10
cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkyl group, a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted
C.sub.1-C.sub.10 heterocycloalkenyl group, a substituted or
unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or
unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or
unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or
unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or
unsubstituted monovalent non-aromatic condensed polycyclic group,
and a substituted or unsubstituted monovalent non-aromatic
condensed heteropolycyclic group.
[0255] For example, R.sub.201 and R.sub.202 in Formula 202 may be
optionally linked (e.g., coupled) via a single bond, a
dimethyl-methylene group, or a diphenyl-methylene group, and
R.sub.203 and R.sub.204 may be optionally linked (e.g., coupled)
via a single bond, a dimethyl-methylene group, or a
diphenyl-methylene group.
[0256] In one embodiment, in Formulae 201 and 202,
[0257] L.sub.201 to L.sub.205 may each independently be selected
from the group consisting of:
[0258] a phenylene group, a pentalenylene group, an indenylene
group, a naphthylene group, an azulenylene group, a heptalenylene
group, an indacenylene group, an acenaphthylene group, a
fluorenylene group, a spiro-bifluorenylene group, a
benzofluorenylene group, a dibenzofluorenylene group, a
phenalenylene group, a phenanthrenylene group, an anthracenylene
group, a fluoranthenylene group, a triphenylenylene group, a
pyrenylene group, a chrysenylene group, a naphthacenylene group, a
picenylene group, a perylenylene group, a pentaphenylene group, a
hexacenylene group, a pentacenylene group, a rubicenylene group, a
coronenylene group, an ovalenylene group, a thiophenylene group, a
furanylene group, a carbazolylene group, an indolylene group, an
isoindolylene group, a benzofuranylene group, a benzothiophenylene
group, a dibenzofuranylene group, a dibenzothiophenylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, a
dibenzosilolylene group, and a pyridinylene group; and
[0259] a phenylene group, a pentalenylene group, an indenylene
group, a naphthylene group, an azulenylene group, a heptalenylene
group, an indacenylene group, an acenaphthylene group, a
fluorenylene group, a spiro-bifluorenylene group, a
benzofluorenylene group, a dibenzofluorenylene group, a
phenalenylene group, a phenanthrenylene group, an anthracenylene
group, a fluoranthenylene group, a triphenylenylene group, a
pyrenylene group, a chrysenylene group, a naphthacenylene group, a
picenylene group, a perylenylene group, a pentaphenylene group, a
hexacenylene group, a pentacenylene group, a rubicenylene group, a
coronenylene group, an ovalenylene group, a thiophenylene group, a
furanylene group, a carbazolylene group, an indolylene group, an
isoindolylene group, a benzofuranylene group, a benzothiophenylene
group, a dibenzofuranylene group, a dibenzothiophenylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, a
dibenzosilolylene group, and a pyridinylene group, each substituted
with at least one selected from deuterium, --F, --Cl, --Br, --I, a
hydroxyl group, a cyano group, a nitro group, an amidino group, a
hydrazino group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group,
a C.sub.1-C.sub.20 alkoxy group, a cyclopentyl group, a cyclohexyl
group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl
group, a phenyl group, a biphenyl group, a terphenyl group, a
phenyl group substituted with a C.sub.1-C.sub.10 alkyl group, a
phenyl group substituted with --F, a pentalenyl group, an indenyl
group, a naphthyl group, an azulenyl group, a heptalenyl group, an
indacenyl group, an acenaphthyl group, a fluorenyl group, a
spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl
group, a phenalenyl group, a phenanthrenyl group, an anthracenyl
group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl
group, a chrysenyl group, a naphthacenyl group, a picenyl group, a
perylenyl group, a pentaphenyl group, a hexacenyl group, a
pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl
group, a thiophenyl group, a furanyl group, a carbazolyl group, an
indolyl group, an isoindolyl group, a benzofuranyl group, a
benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl
group, a benzocarbazolyl group, a dibenzocarbazolyl group, a
dibenzosilolyl group, a pyridinyl group,
--Si(Q.sub.31)(Q.sub.32)(Q.sub.33), and
--N(Q.sub.31)(Q.sub.32),
[0260] wherein Q.sub.31 to Q.sub.33 may each independently be
selected from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
and a naphthyl group.
[0261] In one or more embodiments, xa1 to xa4 may each
independently be an integer selected from 0, 1, or 2.
[0262] In one or more embodiments, xa5 may be 1, 2, 3, or 4.
[0263] In one or more embodiments, R.sub.201 to R.sub.204 and
Q.sub.201 may each independently be selected from a phenyl group, a
biphenyl group, a terphenyl group, a pentalenyl group, an indenyl
group, a naphthyl group, an azulenyl group, a heptalenyl group, an
indacenyl group, an acenaphthyl group, a fluorenyl group, a
spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl
group, a phenalenyl group, a phenanthrenyl group, an anthracenyl
group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl
group, a chrysenyl group, a naphthacenyl group, a picenyl group, a
perylenyl group, a pentaphenyl group, a hexacenyl group, a
pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl
group, a thiophenyl group, a furanyl group, a carbazolyl group, an
indolyl group, an isoindolyl group, a benzofuranyl group, a
benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl
group, a benzocarbazolyl group, a dibenzocarbazolyl group, a
dibenzosilolyl group, and a pyridinyl group; and
[0264] a phenyl group, a biphenyl group, a terphenyl group, a
pentalenyl group, an indenyl group, a naphthyl group, an azulenyl
group, a heptalenyl group, an indacenyl group, an acenaphthyl
group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group,
a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group,
a triphenylenyl group, a pyrenyl group, a chrysenyl group, a
naphthacenyl group, a picenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl
group, a furanyl group, a carbazolyl group, an indolyl group, an
isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a
dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl
group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a
pyridinyl group, each substituted with at least one selected from
deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a cyano group, a
nitro group, an amidino group, a hydrazino group, a hydrazono
group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy
group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl
group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group,
a biphenyl group, a terphenyl group, a phenyl group substituted
with a C.sub.1-C.sub.10 alkyl group, a phenyl group substituted
with --F, a pentalenyl group, an indenyl group, a naphthyl group,
an azulenyl group, a heptalenyl group, an indacenyl group, an
acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group,
a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group,
a triphenylenyl group, a pyrenyl group, a chrysenyl group, a
naphthacenyl group, a picenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl
group, a furanyl group, a carbazolyl group, an indolyl group, an
isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a
dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl
group, a dibenzocarbazolyl group, a dibenzosilolyl group, a
pyridinyl group, --Si(Q.sub.31)(Q.sub.32)(Q.sub.33), and
--N(Q.sub.31)(Q.sub.32), and
[0265] Q.sub.31 to Q.sub.33 may each independently be the same as
described above.
[0266] In one or more embodiments, at least one selected from
R.sub.201 to R.sub.203 in Formula 201 may be selected from the
group consisting of:
[0267] a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl
group, a dibenzofuranyl group, and a dibenzothiophenyl group;
and
[0268] a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl
group, a dibenzofuranyl group, and a dibenzothiophenyl group, each
substituted with at least one selected from deuterium, --F, --Cl,
--Br, --I, a hydroxyl group, a cyano group, a nitro group, an
amidino group, a hydrazino group, a hydrazono group, a
C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a
cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a
cyclopentenyl group, a cyclohexenyl group, a phenyl group, a
biphenyl group, a terphenyl group, a phenyl group substituted with
a C.sub.1-C.sub.10 alkyl group, a phenyl group substituted with
--F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl
group, a carbazolyl group, a dibenzofuranyl group, and a
dibenzothiophenyl group, but embodiments of the present disclosure
are not limited thereto.
[0269] In one or more embodiments, in Formula 202, i) R.sub.201 and
R.sub.202 may be linked (e.g., coupled) via a single bond, and/or
ii) R.sub.203 and R.sub.204 may be linked (e.g., coupled) via a
single bond.
[0270] In one or more embodiments, at least one selected from
R.sub.201 to R.sub.204 in Formula 202 may be selected from the
group consisting of:
[0271] a carbazolyl group; and
[0272] a carbazolyl group substituted with at least one selected
from deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a cyano
group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a cyclopentyl group, a cyclohexyl group, a
cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a
phenyl group, a biphenyl group, a terphenyl group, a phenyl group
substituted with a C.sub.1-C.sub.10 alkyl group, a phenyl group
substituted with --F, a naphthyl group, a fluorenyl group, a
spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl
group, and a dibenzothiophenyl group, but embodiments of the
present disclosure are not limited thereto.
[0273] A compound represented by Formula 201 may be represented by
Formula 201A:
##STR00197##
[0274] For example, the compound represented by Formula 201 may be
represented by Formula 201A(1), but embodiments of the present
disclosure are not limited thereto:
##STR00198##
[0275] In one or more embodiments, the compound represented by
Formula 201 may be represented by Formula 201A-1, but embodiments
of the present disclosure are not limited thereto:
##STR00199##
[0276] A compound represented by Formula 202 may be represented by
Formula 202A:
##STR00200##
[0277] In one or more embodiments, the compound represented by
Formula 202 may be represented by Formula 202A-1:
##STR00201##
[0278] In Formulae 201A, 201A(1), 201A-1, 202A, and 202A-1,
[0279] L.sub.201 to L.sub.203, xa1 to xa3, xa5, and R.sub.202 to
R.sub.204 may each independently be the same as described
above,
[0280] R.sub.211 and R.sub.212 may each independently be the same
as described herein in connection with R.sub.203,
[0281] R.sub.213 to R.sub.217 may each independently be selected
from hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a cyclopentyl group, a cyclohexyl group, a
cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a
phenyl group, a biphenyl group, a terphenyl group, a phenyl group
substituted with a C.sub.1-C.sub.10 alkyl group, a phenyl group
substituted with --F, a pentalenyl group, an indenyl group, a
naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl
group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl
group, a benzofluorenyl group, a dibenzofluorenyl group, a
phenalenyl group, a phenanthrenyl group, an anthracenyl group, a
fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a
chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl
group, a pentaphenyl group, a hexacenyl group, a pentacenyl group,
a rubicenyl group, a coronenyl group, an ovalenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, and a pyridinyl group.
[0282] The hole transport region may include at least one compound
selected from Compounds HT1 to HT39, but embodiments of the
material to be included in the hole transport region are not
limited thereto:
##STR00202## ##STR00203## ##STR00204## ##STR00205## ##STR00206##
##STR00207## ##STR00208## ##STR00209##
[0283] The thickness of the hole transport region may be about 100
.ANG. to about 10,000 .ANG., and in some embodiments, about 100
.ANG. to about 1,000 .ANG.. When the hole transport region includes
at least one selected from a hole injection layer and a hole
transport layer, the thickness of the hole injection layer may be
about 100 .ANG. to about 9,000 .ANG., and in some embodiments,
about 100 .ANG. to about 1,000 .ANG.; the thickness of the hole
transport layer may be about 50 .ANG. to about 2,000 .ANG., and in
some embodiments, about 100 .ANG. to about 1,500 .ANG.. When the
thicknesses of the hole transport region, the hole injection layer,
and the hole transport layer are each within these ranges,
satisfactory hole transporting characteristics may be obtained
without a substantial increase in driving voltage.
[0284] The emission auxiliary layer may increase the light-emission
efficiency of the device by compensating for an optical resonance
distance according to the wavelength of light emitted by an
emission layer (e.g., by adjusting the optical resonance distance
to match the wavelength of light emitted from the emission layer),
and the electron blocking layer may block or reduce the flow of
electrons from an electron transport region. The emission auxiliary
layer and the electron blocking layer may each include those
materials as described above.
p-Dopant
[0285] The hole transport region may further include, in addition
to these materials, a charge-generation material for the
improvement of conductive properties. The charge-generation
material may be homogeneously or non-homogeneously dispersed in the
hole transport region.
[0286] The charge-generation material may be, for example, a
p-dopant.
[0287] The doping concentration of the p-dopant may be 0.1 wt % to
20 wt %, for example, 0.5 wt % to 10 wt %.
[0288] In one embodiment, the p-dopant may have a lowest unoccupied
molecular orbital (LUMO) of -3.5 eV or less.
[0289] The p-dopant may include at least one selected from a
quinone derivative, a metal oxide, and a cyano group-containing
compound, but embodiments of the present disclosure are not limited
thereto.
[0290] For example, the p-dopant may include at least one selected
from the group consisting of:
[0291] a quinone derivative (such as tetracyanoquinodimethane
(TCNQ) and/or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane
(F4-TCNQ));
[0292] a metal oxide (such as tungsten oxide and/or molybdenum
oxide);
[0293] 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN);
and
[0294] a compound represented by Formula 221, but embodiments of
the present disclosure are not limited thereto:
##STR00210##
[0295] In Formula 221,
[0296] R.sub.221 to R.sub.223 may each independently be selected
from a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl
group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkyl group, a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted
C.sub.1-C.sub.10 heterocycloalkenyl group, a substituted or
unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or
unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or
unsubstituted monovalent non-aromatic condensed polycyclic group,
and a substituted or unsubstituted monovalent non-aromatic
condensed heteropolycyclic group, wherein at least one selected
from R.sub.221 to R.sub.223 has at least one substituent selected
from a cyano group, --F, --Cl, --Br, --I, a C.sub.1-C.sub.20 alkyl
group substituted with --F, a C.sub.1-C.sub.20 alkyl group
substituted with --Cl, a C.sub.1-C.sub.20 alkyl group substituted
with --Br, and a C.sub.1-C.sub.20 alkyl group substituted with
--I.
Emission Layer in Organic Layer 150
[0297] When the organic light-emitting device 10 is a full color
organic light-emitting device, the emission layer may be patterned
into a red emission layer, a green emission layer, and/or a blue
emission layer, according to a sub pixel. In one or more
embodiments, the emission layer may have a stacked structure of two
or more layers selected from a red emission layer, a green emission
layer, and a blue emission layer, in which the two or more layers
may contact each other or may be separated from each other. In one
or more embodiments, the emission layer may include two or more
materials selected from a red-light emission material, a
green-light emission material, and a blue-light emission material,
in which the two or more materials may be mixed together in a
single layer to thereby emit white light.
[0298] In one embodiment, the emission layer of the organic
light-emitting device 10 may be a first-color-light
emitting-emission layer,
[0299] the organic light-emitting device 10 may further include i)
at least one second-color-light emitting-emission layer, or ii) at
least one second-color-light emitting-emission layer and at least
one third-color-light emitting-emission layer, each between the
first electrode 110 and the second electrode 190,
[0300] a maximum emission wavelength of the first-color-light
emitting-emission layer, a maximum emission wavelength of the
second-color-light emitting-emission layer, and a maximum emission
wavelength of the third-color-light emitting-emission layer may be
identical to or different from each other, and
[0301] the organic light-emitting device 10 may emit a mixed light
including a first-color-light and a second-color-light, or a mixed
light including the first-color-light, the second-color-light, and
a third-color-light, but embodiments of the present disclosure are
not limited thereto.
[0302] For example, the maximum emission wavelength of the
first-color-light emitting-emission layer may be different from the
maximum emission wavelength of the second-color-light
emitting-emission layer, and the mixed light including the
first-color-light and the second-color-light may be white light,
but embodiments of the present disclosure are not limited
thereto.
[0303] In one or more embodiments, the maximum emission wavelength
of the first-color-light emitting-emission layer, the maximum
emission wavelength of the second-color-light emitting-emission
layer, and the maximum emission wavelength of the third-color-light
emitting-emission layer may be different from one another, and the
mixed light including the first-color-light, the
second-color-light, and the third-color-light may be white light.
However, embodiments of the present disclosure are not limited
thereto.
[0304] The emission layer may include a host and a dopant. The
dopant may include at least one selected from a phosphorescent
dopant and a fluorescent dopant.
[0305] The amount of the dopant in the emission layer may be about
0.01 to about 15 parts by weight based on 100 parts by weight of
the host, but embodiments of the present disclosure are not limited
thereto.
[0306] The thickness of the emission layer may be about 100 .ANG.
to about 1,000 .ANG., and in some embodiments, about 200 .ANG. to
about 600 .ANG.. When the thickness of the emission layer is within
these ranges, excellent light-emission characteristics may be
obtained without a substantial increase in driving voltage.
Host in Emission Layer
[0307] The emission layer may include the first compound
represented by one selected from Formulae 1A to 1E as a host. The
first compound may be the same as described above.
[0308] The emission layer may include the first compound
represented by one selected from Formulae 1A to 1E as a first host,
and may further include a second host that is different from the
first host.
[0309] For example, the second host may be selected from compounds
described above as an example of the first compound represented by
one selected from Formulae 1A to 1E.
[0310] In one or more embodiments, the second host may be selected
from 9,10-di(2-naphthyl)anthracene (ADN),
2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),
9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN),
4,4'-bis(N-carbazolyl)-1,1-biphenyl (CBP),
1,3-di-9-carbazolylbenzene (mCP), and
1,3,5-tri(carbazol-9-yl)benzene (TCP), but embodiments of the
present disclosure are not limited thereto.
[0311] A weight ratio of the first host to the second host in the
emission layer may be, for example, 90:10 to 10:90, and in some
embodiments, 80:20 to 20:80, and in some embodiments, 50:50, but
embodiments of the present disclosure are not limited thereto.
Phosphorescent Dopant Included in Emission Layer in Organic Layer
150
[0312] The phosphorescent dopant may include an organometallic
complex represented by Formula 401 below:
##STR00211##
[0313] In Formulae 401 and 402,
[0314] M may be selected from iridium (Ir), platinum (Pt),
palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium
(Hf), europium (Eu), terbium (Tb), rhodium (Rh), and thulium
(Tm),
[0315] L.sub.401 may be a ligand represented by Formula 402, xc1
may be 1, 2, or 3, and when xc1 is two or more, two or more
L.sub.401(s) may be identical to or different from each other,
[0316] L.sub.402 may be an organic ligand, xc2 may be an integer
selected from 0 to 4, and when xc2 is two or more, two or more
L.sub.402(s) may be identical to or different from each other,
[0317] X.sub.401 to X.sub.404 may each independently be nitrogen or
carbon,
[0318] X.sub.401 may be linked to (e.g., coupled) to X.sub.403 via
a single bond or a double bond, and X.sub.402 may be linked to
(e.g., coupled) to X.sub.404 via a single bond or a double
bond,
[0319] A.sub.401 and A.sub.402 may each independently be a
C.sub.5-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60
heterocyclic group,
[0320] X.sub.405 may be a single bond, *--O--*', *--S--*',
*--C(.dbd.O)--*', *--N(Q.sub.411)-*',
*--C(Q.sub.411)(Q.sub.412)-*', *--C(Q.sub.411)=C(Q.sub.412)-*',
*--C(Q.sub.411)=*', or *.dbd.C(Q.sub.411)=*', and Q.sub.411 and
Q.sub.412 may each independently be hydrogen, deuterium, a
C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a
phenyl group, a biphenyl group, a terphenyl group, or a naphthyl
group,
[0321] X.sub.406 may be a single bond, O, or S,
[0322] R.sub.401 and R.sub.402 may each independently be selected
from hydrogen, deuterium, --F, --Cl, --Br, --I, --CD.sub.3,
--CF.sub.3, a hydroxyl group, a cyano group, a nitro group, an
amidino group, a hydrazino group, a hydrazono group, a substituted
or unsubstituted C.sub.1-C.sub.20 alkyl group, a substituted or
unsubstituted C.sub.1-C.sub.20 alkoxy group, a substituted or
unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or
unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a
substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a
substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl
group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group,
a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a
substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a
substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a
substituted or unsubstituted monovalent non-aromatic condensed
polycyclic group and a substituted or unsubstituted monovalent
non-aromatic condensed heteropolycyclic group
--Si(Q.sub.401)(Q.sub.402)(Q.sub.403), --N(Q.sub.401)(Q.sub.402),
--B(Q.sub.401)(Q.sub.402), --C(.dbd.O)(Q.sub.401),
--S(.dbd.O).sub.2(Q.sub.401), and
--P(.dbd.O)(Q.sub.401)(Q.sub.402), wherein Q.sub.401 to Q.sub.403
may each independently be selected from a C.sub.1-C.sub.10 alkyl
group, a C.sub.1-C.sub.10 alkoxy group, a C.sub.6-C.sub.20 aryl
group, and a C.sub.1-C.sub.20 heteroaryl group,
[0323] xc11 and xc12 may each independently be an integer selected
from 0 to 10, and
[0324] * and *' in Formula 402 may each independently indicate a
binding site to M in Formula 401.
[0325] In one embodiment, A.sub.401 and A.sub.402 in Formula 402
may each independently be selected from a benzene group, a
naphthalene group, a fluorene group, a spiro-bifluorene group, an
indene group, a pyrrole group, a thiophene group, a furan group, an
imidazole group, a pyrazole group, a thiazole group, an isothiazole
group, an oxazole group, an isoxazole group, a pyridine group, a
pyrazine group, a pyrimidine group, a pyridazine group, a quinoline
group, an isoquinoline group, a benzoquinoline group, a quinoxaline
group, a quinazoline group, a carbazole group, a benzimidazole
group, a benzofuran group, a benzothiophene group, an
isobenzothiophene group, a benzoxazole group, an isobenzoxazole
group, a triazole group, a tetrazole group, an oxadiazole group, a
triazine group, a dibenzofuran group, and a dibenzothiophene
group.
[0326] In one or more embodiments, in Formula 402, i) X.sub.401 may
be nitrogen, and X.sub.402 may be carbon, or ii) X.sub.401 and
X.sub.402 may both (e.g., simultaneously) be nitrogen.
[0327] In one or more embodiments, R.sub.401 and R.sub.402 in
Formula 402 may each independently be selected from the group
consisting of:
[0328] hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group,
a cyano group, a nitro group, an amidino group, a hydrazino group,
a hydrazono group, a C.sub.1-C.sub.20 alkyl group, and a
C.sub.1-C.sub.20 alkoxy group;
[0329] a C.sub.1-C.sub.20 alkyl group and a C.sub.1-C.sub.20 alkoxy
group, each substituted with at least one selected from deuterium,
--F, --Cl, --Br, --I, a hydroxyl group, a cyano group, a nitro
group, an amidino group, a hydrazino group, a hydrazono group, a
phenyl group, a naphthyl group, a cyclopentyl group, a cyclohexyl
group, an adamantyl group, a norbornanyl group, and a norbornenyl
group;
[0330] a cyclopentyl group, a cyclohexyl group, an adamantyl group,
a norbornanyl group, a norbornenyl group, a phenyl group, a
biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl
group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a
pyridazinyl group, a triazinyl group, a quinolinyl group, an
isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a
carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl
group;
[0331] a cyclopentyl group, a cyclohexyl group, an adamantyl group,
a norbornanyl group, a norbornenyl group a phenyl group, a biphenyl
group, a terphenyl group, a naphthyl group, a fluorenyl group, a
pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a
pyridazinyl group, a triazinyl group, a quinolinyl group, an
isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a
carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl
group, each substituted with at least one selected from deuterium,
--F, --Cl, --Br, --I, a hydroxyl group, a cyano group, a nitro
group, an amidino group, a hydrazino group, a hydrazono group, a
C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a
cyclopentyl group, a cyclohexyl group, an adamantyl group, a
norbornanyl group, a norbornenyl group, a phenyl group, a biphenyl
group, a terphenyl group, a naphthyl group, a fluorenyl group, a
pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a
pyridazinyl group, a triazinyl group, a quinolinyl group, an
isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a
carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl
group; and
[0332] --Si(Q.sub.401)(Q.sub.402)(Q.sub.403),
--N(Q.sub.401)(Q.sub.402), --B(Q.sub.401)(Q.sub.402),
--C(.dbd.O)(Q.sub.401), --S(.dbd.O).sub.2(Q.sub.401), and
--P(.dbd.O)(Q.sub.401)(Q.sub.402),
[0333] wherein Q.sub.401 to Q.sub.403 may each independently be
selected from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10
alkoxy group, a phenyl group, a biphenyl group, and a naphthyl
group, but embodiments of the present disclosure are not limited
thereto.
[0334] In one or more embodiments, when xc1 in Formula 401 is two
or more, two A.sub.401(s) in two or more L.sub.401(s) may be
optionally linked (e.g., coupled) via a linking group X.sub.407,
and two A.sub.402(s) in two or more L.sub.401(s) may be optionally
linked (e.g., coupled) via a linking group X.sub.408 (see Compounds
PD1 to PD4 and PD7). X.sub.407 and X.sub.408 may each independently
be a single bond, *--O--*', *--S--*', *--C(.dbd.O)--*',
*--N(Q.sub.413)-*', *--C(Q.sub.413)(Q.sub.414)-*', or
*--C(Q.sub.413)=C(Q.sub.414)-*' (wherein Q.sub.413 and Q.sub.414
may each independently be hydrogen, deuterium, a C.sub.1-C.sub.20
alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a
biphenyl group, a terphenyl group, or a naphthyl group), but
embodiments of the present disclosure are not limited thereto.
[0335] L.sub.402 in Formula 401 may be a monovalent, divalent, or
trivalent organic ligand. For example, L.sub.402 may be selected
from halogen, diketone (for example, acetylacetonate), a carboxylic
acid (for example, picolinate), --C(.dbd.O), an isonitrile, --CN,
and a phosphorus-based ligand (for example, phosphine or
phosphite), but embodiments of the present disclosure are not
limited thereto.
[0336] In one or more embodiments, the phosphorescent dopant may be
selected from, for example, Compounds PD1 to PD25, but embodiments
of the present disclosure are not limited thereto:
##STR00212## ##STR00213## ##STR00214## ##STR00215## ##STR00216##
##STR00217##
Fluorescent Dopant in Emission Layer
[0337] The fluorescent dopant may include an arylamine compound or
a styrylamine compound.
[0338] In one or more embodiments, the fluorescent dopant may
include a compound represented by Formula 501:
##STR00218##
[0339] In Formula 501,
[0340] Ar.sub.501 may be a substituted or unsubstituted
C.sub.5-C.sub.60 carbocyclic group or a substituted or
unsubstituted C.sub.1-C.sub.60 heterocyclic group,
[0341] L.sub.501 to L.sub.503 may each independently be selected
from a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkylene
group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkylene group, a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkenylene group, a substituted or
unsubstituted C.sub.1-C.sub.10 heterocycloalkenylene group, a
substituted or unsubstituted C.sub.6-C.sub.60 arylene group, a
substituted or unsubstituted C.sub.1-C.sub.60 heteroarylene group,
a substituted or unsubstituted divalent non-aromatic condensed
polycyclic group, and a substituted or unsubstituted divalent
non-aromatic condensed heteropolycyclic group,
[0342] xd1 to xd3 may each independently be an integer selected
from 0 to 3,
[0343] R.sub.501 and R.sub.502 may each independently be selected
from a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl
group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkyl group, a substituted or unsubstituted
C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted
C.sub.1-C.sub.10 heterocycloalkenyl group, a substituted or
unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or
unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or
unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or
unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or
unsubstituted monovalent non-aromatic condensed polycyclic group,
and a substituted or unsubstituted monovalent non-aromatic
condensed heteropolycyclic group,
[0344] xd4 may be an integer selected from 1 to 6.
[0345] In one embodiment, Ar.sub.501 in Formula 501 may be selected
from the group consisting of:
[0346] a naphthalene group, a heptalene group, a fluorene group, a
spiro-bifluorene group, a benzofluorene group, a dibenzofluorene
group, a phenalene group, a phenanthrene group, an anthracene
group, a fluoranthene group, a triphenylene group, a pyrene group,
a chrysene group, naphthacene group, a picene group, a perylene
group, a pentaphene group, an indenoanthracene group, and an
indenophenanthrene group; and
[0347] a naphthalene group, a heptalene group, a fluorene group, a
spiro-bifluorene group, a benzofluorene group, a dibenzofluorene
group, a phenalene group, a phenanthrene group, an anthracene
group, a fluoranthene group, a triphenylene group, a pyrene group,
a chrysene group, naphthacene group, a picene group, a perylene
group, a pentaphene group, an indenoanthracene group, and an
indenophenanthrene group, each substituted with at least one
selected from deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
and a naphthyl group.
[0348] In one or more embodiments, L.sub.501 to L.sub.503 in
Formula 501 may each independently be selected from a phenylene
group, a naphthylene group, a fluorenylene group, a
spiro-bifluorenylene group, a benzofluorenylene group, a
dibenzofluorenylene group, a phenanthrenylene group, an
anthracenylene group, a fluoranthenylene group, a triphenylenylene
group, a pyrenylene group, a chrysenylene group, a perylenylene
group, a pentaphenylene group, a hexacenylene group, a
pentacenylene group, a thiophenylene group, a furanylene group, a
carbazolylene group, an indolylene group, an isoindolylene group, a
benzofuranylene group, a benzothiophenylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, a
dibenzosilolylene group, and a pyridinylene group; and
[0349] a phenylene group, a naphthylene group, a fluorenylene
group, a spiro-bifluorenylene group, a benzofluorenylene group, a
dibenzofluorenylene group, a phenanthrenylene group, an
anthracenylene group, a fluoranthenylene group, a triphenylenylene
group, a pyrenylene group, a chrysenylene group, a perylenylene
group, a pentaphenylene group, a hexacenylene group, a
pentacenylene group, a thiophenylene group, a furanylene group, a
carbazolylene group, an indolylene group, an isoindolylene group, a
benzofuranylene group, a benzothiophenylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, a
dibenzosilolylene group, and a pyridinylene group, each substituted
with at least one selected from deuterium, --F, --Cl, --Br, --I, a
hydroxyl group, a cyano group, a nitro group, an amidino group, a
hydrazino group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group,
a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group,
a terphenyl group, a naphthyl group, a fluorenyl group, a
spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl
group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl
group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a
perylenyl group, a pentaphenyl group, a hexacenyl group, a
pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl
group, an indolyl group, an isoindolyl group, a benzofuranyl group,
a benzothiophenyl group, a dibenzofuranyl group, a
dibenzothiophenyl group, a benzocarbazolyl group, a
dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl
group.
[0350] In one or more embodiments, R.sub.501 and R.sub.502 in
Formula 501 may each independently be selected from the group
consisting of:
[0351] a phenyl group, a biphenyl group, a terphenyl group, a
naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, and a pyridinyl group; and
[0352] a phenyl group, a biphenyl group, a terphenyl group, a
naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, and a pyridinyl group, each substituted with at least one
selected from deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, a pyridinyl group, and
--Si(Q.sub.31)(Q.sub.32)(Q.sub.33),
[0353] wherein Q.sub.31 to Q.sub.33 may each independently be
selected from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
and a naphthyl group.
[0354] In one or more embodiments, xd4 in Formula 501 may be 2, but
embodiments of the present disclosure are not limited thereto.
[0355] For example, the fluorescent dopant may be selected from
Compounds FD1 to FD22:
##STR00219## ##STR00220## ##STR00221## ##STR00222##
[0356] In one or more embodiments, the fluorescent dopant may be
selected from the following compounds, but embodiments of the
present disclosure are not limited thereto:
##STR00223##
Electron Transport Region in Organic Layer 150
[0357] The electron transport region may have: i) a single-layered
structure including a single layer including a single material, ii)
a single-layered structure including a single layer including a
plurality of different materials, or iii) a multi-layered structure
having a plurality of layers including a plurality of different
materials.
[0358] The electron transport region may include at least one
selected from a buffer layer, a hole blocking layer, an electron
control layer, an electron transport layer (ETL), and an electron
injection layer, but embodiments of the present disclosure are not
limited thereto.
[0359] For example, the electron transport region may have a
structure of electron transport layer/electron injection layer, a
structure of hole blocking layer/electron transport layer/electron
injection layer, a structure of electron control layer/electron
transport layer/electron injection layer, or a structure of buffer
layer/electron transport layer/electron injection layer, wherein
layers of each structure are sequentially stacked on the emission
layer in each stated order. However, embodiments of the structure
of the electron transport layer are not limited thereto.
[0360] The electron transport region may include the second
compound represented by Formula 2A or 2B as described above.
[0361] In one embodiment, the electron transport region may include
an buffer layer, the buffer layer may directly contact the emission
layer, and the buffer layer may include the second compound
represented by Formula 2A or 2B as described above.
[0362] In one or more embodiments, the electron transport region
may include a buffer layer, an electron layer, and an electron
injection layer stacked in this stated order on the emission layer,
and the buffer layer may include the second compound represented by
Formula 2A or 2B as described above.
[0363] The electron transport region (for example, a hole blocking
layer, an electron control layer, and/or an electron transport
layer in the electron transport region) may include a metal-free
compound containing at least one .pi. electron-depleted
nitrogen-containing ring.
[0364] As used herein, the term ".pi. electron-depleted
nitrogen-containing ring" indicates a C.sub.1-C.sub.60 heterocyclic
group having at least one *--N.dbd.*' moiety as a ring-forming
moiety.
[0365] For example, the ".pi. electron-depleted nitrogen-containing
ring" may be i) a 5-membered to 7-membered heteromonocyclic group
having at least one *--N.dbd.*' moiety, ii) a heteropolycyclic
group in which two or more 5-membered to 7-membered
heteromonocyclic groups each having at least one *--N.dbd.*' moiety
are condensed with each other, or iii) a heteropolycyclic group in
which at least one 5-membered to 7-membered heteromonocyclic group
having at least one *--N.dbd.*' moiety is condensed with at least
one C.sub.5-C.sub.60 carbocyclic group.
[0366] Non-limiting examples of the .pi. electron-depleted
nitrogen-containing ring may include an imidazole, a pyrazole, a
thiazole, an isothiazole, an oxazole, an isoxazole, a pyridine, a
pyrazine, a pyrimidine, a pyridazine, an indazole, a purine, a
quinoline, an isoquinoline, a benzoquinoline, a phthalazine, a
naphthyridine, a quinoxaline, a quinazoline, a cinnoline, a
phenanthridine, an acridine, a phenanthroline, a phenazine, a
benzimidazole, an isobenzothiazole, a benzoxazole, an
isobenzoxazole, a triazole, a tetrazole, an oxadiazole, a triazine,
a thiadiazole, an imidazopyridine, an imidazopyrimidine, and an
azacarbazole, but embodiments of the present disclosure are not
limited thereto.
[0367] For example, the electron transport region may include a
compound represented by Formula 601:
[Ar.sub.601].sub.xe11-[(L.sub.601).sub.xe1-R.sub.601].sub.xe21.
Formula 601
[0368] In Formula 601,
[0369] Ar.sub.601 may be a substituted or unsubstituted
C.sub.5-C.sub.60 carbocyclic group or a substituted or
unsubstituted C.sub.1-C.sub.60 heterocyclic group,
[0370] xe11 may be 1, 2, or 3,
[0371] L.sub.601 may be selected from a substituted or
unsubstituted C.sub.3-C.sub.10 cycloalkylene group, a substituted
or unsubstituted C.sub.1-C.sub.10 heterocycloalkylene group, a
substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenylene
group, a substituted or unsubstituted C.sub.1-C.sub.10
heterocycloalkenylene group, a substituted or unsubstituted
C.sub.6-C.sub.60 arylene group, a substituted or unsubstituted
C.sub.1-C.sub.60 heteroarylene group, a substituted or
unsubstituted divalent non-aromatic condensed polycyclic group, and
a substituted or unsubstituted divalent non-aromatic condensed
heteropolycyclic group,
[0372] xe1 may be an integer selected from 0 to 5,
[0373] R.sub.601 may be selected from a substituted or
unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or
unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a
substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a
substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl
group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group,
a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a
substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a
substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a
substituted or unsubstituted monovalent non-aromatic condensed
polycyclic group, a substituted or unsubstituted monovalent
non-aromatic condensed heteropolycyclic group,
--Si(Q.sub.601)(Q.sub.602)(Q.sub.603), --C(.dbd.O)(Q.sub.601),
--S(.dbd.O).sub.2(Q.sub.601), and
--P(.dbd.O)(Q.sub.601)(Q.sub.602),
[0374] Q.sub.601 to Q.sub.603 may each independently be a
C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a
phenyl group, a biphenyl group, a terphenyl group, or a naphthyl
group, and
[0375] xe21 may be an integer selected from 1 to 5.
[0376] In one embodiment, at least one of the xe11 Ar.sub.601(s)
and/or at least one of the xe21 R.sub.601(s) may include the .pi.
electron-depleted nitrogen-containing ring.
[0377] In one embodiment, ring Ar.sub.601 in Formula 601 may be
selected from the group consisting of:
[0378] a benzene group, a naphthalene group, a fluorene group, a
spiro-bifluorene group, a benzofluorene group, a dibenzofluorene
group, a phenalene group, a phenanthrene group, an anthracene
group, a fluoranthene group, a triphenylene group, a pyrene group,
a chrysene group, naphthacene group, a picene group, a perylene
group, a pentaphene group, an indenoanthracene group, a
dibenzofuran group, a dibenzothiophene group, a carbazole group, an
imidazole group, a pyrazole group, a thiazole group, an isothiazole
group, an oxazole group, an isoxazole group, a pyridine group, a
pyrazine group, a pyrimidine group, a pyridazine group, an indazole
group, a purine group, a quinoline group, an isoquinoline group, a
benzoquinoline group, a phthalazine group, naphthyridine group, a
quinoxaline group, a quinazoline group, a cinnoline group, a
phenanthridine group, an acridine group, a phenanthroline group, a
phenazine group, a benzimidazole group, an iso-benzothiazole group,
a benzoxazole group, an isobenzoxazole group, a triazole group, a
tetrazole group, an oxadiazole group, a triazine group, thiadiazole
group, an imidazopyridine group, an imidazopyrimidine group, and an
azacarbazole group; and
[0379] a benzene group, a naphthalene group, a fluorene group, a
spiro-bifluorene group, a benzofluorene group, a dibenzofluorene
group, a phenalene group, a phenanthrene group, an anthracene
group, a fluoranthene group, a triphenylene group, a pyrene group,
a chrysene group, naphthacene group, a picene group, a perylene
group, a pentaphene group, an indenoanthracene group, a
dibenzofuran group, a dibenzothiophene group, a carbazole group, an
imidazole group, a pyrazole group, a thiazole group, an isothiazole
group, an oxazole group, an isoxazole group, a pyridine group, a
pyrazine group, a pyrimidine group, a pyridazine group, an indazole
group, a purine group, a quinoline group, an isoquinoline group, a
benzoquinoline group, a phthalazine group, naphthyridine group, a
quinoxaline group, a quinazoline group, a cinnoline group, a
phenanthridine group, an acridine group, a phenanthroline group, a
phenazine group, a benzimidazole group, an iso-benzothiazole group,
a benzoxazole group, an isobenzoxazole group, a triazole group, a
tetrazole group, an oxadiazole group, a triazine group, thiadiazole
group, an imidazopyridine group, an imidazopyrimidine group, and an
azacarbazole group, each substituted with at least one selected
from deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a cyano
group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
a naphthyl group, --Si(Q.sub.31)(Q.sub.32)(Q.sub.33),
--S(.dbd.O).sub.2(Q.sub.31), and
--P(.dbd.O)(Q.sub.31)(Q.sub.32),
[0380] wherein Q.sub.31 to Q.sub.33 may each independently be
selected from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
and a naphthyl group.
[0381] When xe11 in Formula 601 is two or more, two or more
Ar.sub.601(s) may be linked (e.g., coupled) via one or more single
bonds.
[0382] In one or more embodiments, Ar.sub.601 in Formula 601 may be
an anthracene group.
[0383] In one or more embodiments, a compound represented by
Formula 601 may be represented by Formula 601-1:
##STR00224##
[0384] In Formula 601-1,
[0385] X.sub.614 may be N or C(R.sub.614), X.sub.615 may be N or
C(R.sub.615), X.sub.616 may be N or C(R.sub.616), and at least one
selected from X.sub.614 to X.sub.616 may be N,
[0386] L.sub.611 to L.sub.613 may each independently be the same as
described herein in connection with L.sub.601,
[0387] xe611 to xe613 may each independently be the same as
described herein in connection with xe1,
[0388] R.sub.611 to R.sub.613 may each independently be the same as
described herein in connection with R.sub.601,
[0389] R.sub.614 to R.sub.616 may each independently be selected
from hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
and a naphthyl group.
[0390] In one embodiment, L.sub.601 and L.sub.611 to L.sub.613 in
Formulae 601 and 601-1 may each independently be selected from the
group consisting of:
[0391] a phenylene group, a naphthylene group, a fluorenylene
group, a spiro-bifluorenylene group, a benzofluorenylene group, a
dibenzofluorenylene group, a phenanthrenylene group, an
anthracenylene group, a fluoranthenylene group, a triphenylenylene
group, a pyrenylene group, a chrysenylene group, a perylenylene
group, a pentaphenylene group, a hexacenylene group, a
pentacenylene group, a thiophenylene group, a furanylene group, a
carbazolylene group, an indolylene group, an isoindolylene group, a
benzofuranylene group, a benzothiophenylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, a
dibenzosilolylene group, a pyridinylene group, an imidazolylene
group, a pyrazolylene group, a thiazolylene group, an
isothiazolylene group, an oxazolylene group, an isoxazolylene
group, a thiadiazolylene group, an oxadiazolylene group, a
pyrazinylene group, a pyrimidinylene group, a pyridazinylene group,
a triazinylene group, a quinolinylene group, an isoquinolinylene
group, a benzoquinolinylene group, a phthalazinylene group, a
naphthyridinylene group, a quinoxalinylene group, a quinazolinylene
group, a cinnolinylene group, a phenanthridinylene group, an
acridinylene group, a phenanthrolinylene group, a phenazinylene
group, a benzimidazolylene group, an isobenzothiazolylene group, a
benzoxazolylene group, an isobenzoxazolylene group, a triazolylene
group, a tetrazolylene group, an imidazopyridinylene group, an
imidazopyrimidinylene group, and an azacarbazolylene group; and
[0392] a phenylene group, a naphthylene group, a fluorenylene
group, a spiro-bifluorenylene group, a benzofluorenylene group, a
dibenzofluorenylene group, a phenanthrenylene group, an
anthracenylene group, a fluoranthenylene group, a triphenylenylene
group, a pyrenylene group, a chrysenylene group, a perylenylene
group, a pentaphenylene group, a hexacenylene group, a
pentacenylene group, a thiophenylene group, a furanylene group, a
carbazolylene group, an indolylene group, an isoindolylene group, a
benzofuranylene group, a benzothiophenylene group, a
dibenzofuranylene group, a dibenzothiophenylene group, a
benzocarbazolylene group, a dibenzocarbazolylene group, a
dibenzosilolylene group, a pyridinylene group, an imidazolylene
group, a pyrazolylene group, a thiazolylene group, an
isothiazolylene group, an oxazolylene group, an isoxazolylene
group, a thiadiazolylene group, an oxadiazolylene group, a
pyrazinylene group, a pyrimidinylene group, a pyridazinylene group,
a triazinylene group, a quinolinylene group, an isoquinolinylene
group, a benzoquinolinylene group, a phthalazinylene group, a
naphthyridinylene group, a quinoxalinylene group, a quinazolinylene
group, a cinnolinylene group, a phenanthridinylene group, an
acridinylene group, a phenanthrolinylene group, a phenazinylene
group, a benzimidazolylene group, an isobenzothiazolylene group, a
benzoxazolylene group, an isobenzoxazolylene group, a triazolylene
group, a tetrazolylene group, an imidazopyridinylene group, an
imidazopyrimidinylene group, and an azacarbazolylene group, each
substituted with at least one selected from deuterium, --F, --Cl,
--Br, --I, a hydroxyl group, a cyano group, a nitro group, an
amidino group, a hydrazino group, a hydrazono group, a
C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a
phenyl group, a biphenyl group, a terphenyl group, a naphthyl
group, a fluorenyl group, a spiro-bifluorenyl group, a
banzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a peryenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzoccarbazolyl group, a dibenzosilolyl
group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, an isothiazolyl group, an oxazolyl group, an
isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a
triazinyl group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl
group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl
group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group,
an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
imidazopyridinyl group, an imidazopyrimidinyl group, and an
azacarbazolyl group, but embodiments of the present disclosure are
not limited thereto.
[0393] In one or more embodiments, xe1 and xe611 to xe613 in
Formulae 601 and 601-1 may each independently be 0, 1, or 2.
[0394] In one or more embodiments, R.sub.601 and R.sub.611 to
R.sub.613 in Formula 601 and 601-1 may each independently be
selected from the group consisting of:
[0395] a phenyl group, a biphenyl group, a terphenyl group, a
naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, an isothiazolyl group, an oxazolyl group, an
isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a
triazinyl group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl
group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl
group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group,
an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
imidazopyridinyl group, an imidazopyrimidinyl group, and an
azacarbazolyl group;
[0396] a phenyl group, a biphenyl group, a terphenyl group, a
naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, an isothiazolyl group, an oxazolyl group, an
isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a
triazinyl group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl
group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl
group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group,
an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
imidazopyridinyl group, an imidazopyrimidinyl group, and an
azacarbazolyl group, each substituted with at least one selected
from deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a cyano
group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20
alkoxy group, a phenyl group, a biphenyl group, a terphenyl group,
a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a
benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl
group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyrenyl group, a chrysenyl group, a perylenyl group, a
pentaphenyl group, a hexacenyl group, a pentacenyl group, a
thiophenyl group, a furanyl group, a carbazolyl group, an indolyl
group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl
group, a dibenzofuranyl group, a dibenzothiophenyl group, a
benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl
group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a
thiazolyl group, an isothiazolyl group, an oxazolyl group, an
isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a
pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a
triazinyl group, a quinolinyl group, an isoquinolinyl group, a
benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl
group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl
group, a phenanthridinyl group, an acridinyl group, a
phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group,
an isobenzothiazolyl group, a benzoxazolyl group, an
isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an
imidazopyridinyl group, an imidazopyrimidinyl group, and an
azacarbazolyl group; and
[0397] --S(.dbd.O).sub.2(Q.sub.601) and
--P(.dbd.O)(Q.sub.601)(Q.sub.602),
[0398] wherein Q.sub.601 and Q.sub.602 may each independently be
the same as described above.
[0399] The electron transport region may include at least one
compound selected from Compounds ET1 to ET36, but embodiments of
the present disclosure are not limited thereto:
##STR00225## ##STR00226## ##STR00227## ##STR00228## ##STR00229##
##STR00230## ##STR00231##
[0400] In one or more embodiments, the electron transport region
may include at least one selected from BCP
(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), BPhen
(4,7-diphenyl-1,10-phenanthroline), Alq.sub.3, BAlq,
TAZ(3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole),
and NTAZ.
##STR00232##
[0401] The thicknesses of the buffer layer, the hole blocking
layer, and/or the electron controlling layer may each independently
be about 20 .ANG. to about 1,000 .ANG., and in some embodiments,
about 30 .ANG. to about 300 .ANG.. When the thicknesses of the
buffer layer, the hole blocking layer, and the electron control
layer are each within these ranges, the electron blocking layer may
have excellent electron blocking characteristics and/or electron
control characteristics without a substantial increase in driving
voltage.
[0402] The thickness of the electron transport layer may be about
100 .ANG. to about 1,000 .ANG., and in some embodiments, about 150
.ANG. to about 500 .ANG.. When the thickness of the electron
transport layer is within these ranges, the electron transport
layer may have satisfactory electron transport characteristics
without a substantial increase in driving voltage.
[0403] The electron transport region (for example, the electron
transport layer in the electron transport region) may further
include, in addition to the materials described above, a
metal-containing material.
[0404] The metal-containing material may include at least one
selected from an alkali metal complex and an alkaline earth metal
complex. The alkali metal complex may include a metal ion selected
from a lithium (Li) ion, a sodium (Na) ion, a potassium (K) ion, a
rubidium (Rb) ion, and a cesium (Cs) ion, and the alkaline earth
metal complex may include a metal ion selected from a beryllium
(Be) ion, a magnesium (Mg) ion, a calcium (Ca) ion, a strontium
(Sr) ion, and a barium (Ba) ion. Each ligand coordinated with the
metal ion of the alkali metal complex or the alkaline earth metal
complex may independently be selected from a hydroxyquinoline, a
hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a
hydroxyphenanthridine, a hydroxyphenyl oxazole, a hydroxyphenyl
thiazole, a hydroxydiphenyl oxadiazole, a hydroxydiphenyl
thiadiazole, a hydroxyphenyl pyridine, a hydroxyphenyl
benzimidazole, a hydroxyphenyl benzothiazole, a bipyridine, a
phenanthroline, and a cyclopentadiene, but embodiments of the
present disclosure are not limited thereto.
[0405] For example, the metal-containing material may include a Li
complex. The Li complex may include, for example, Compound ET-D1
(lithium quinolate, LiQ) and/or ET-D2.
##STR00233##
[0406] The electron transport region may include an electron
injection layer that facilitates injection of electrons from the
second electrode 190. The electron injection layer may directly
contact the second electrode 190.
[0407] The electron injection layer may have i) a single-layered
structure including a single layer including a single material, ii)
a single-layered structure including a single layer including a
plurality of different materials, or iii) a multi-layered structure
having a plurality of layers including a plurality of different
materials.
[0408] The electron injection layer may include an alkali metal, an
alkaline earth metal, a rare earth metal, an alkali metal compound,
an alkaline earth metal compound, a rare earth metal compound, an
alkali metal complex, an alkaline earth metal complex, a rare earth
metal complex, or a combination thereof.
[0409] In one or more embodiments, the electron injection layer may
include Li, Na, K, rubidium (Rb), cesium (Cs), Mg, Ca, erbium (Er),
thulium (Tm), ytterbium (Yb), or a combination thereof. However,
embodiments of the material included in the electron injection
layer are not limited thereto.
[0410] The alkali metal may be selected from Li, Na, K, Rb, and Cs.
In one embodiment, the alkali metal may be Li, Na, or Cs. In one or
more embodiments, the alkali metal may be Li or Cs, but embodiments
of the present disclosure are not limited thereto.
[0411] The alkaline earth metal may be selected from Mg, Ca, Sr,
and Ba.
[0412] The rare earth metal may be selected from scandium (Sc),
yttrium (Y), cerium (Ce), ytterbium (Yb), gadolinium (Gd), and
terbium (Tb).
[0413] The alkali metal compound, the alkaline earth metal
compound, and the rare earth metal compound may be selected from
oxides and halides (for example, fluorides, chlorides, bromides,
and/or iodides) of the alkali metal, the alkaline earth metal, and
the rare earth metal.
[0414] The alkali metal compound may be selected from alkali metal
oxides (such as Li.sub.2O, Cs.sub.2O, and/or K.sub.2O) and alkali
metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, RbI,
and/or KI). In one embodiment, the alkali metal compound may be
selected from LiF, Li.sub.2O, NaF, LiI, NaI, CsI, and KI, but
embodiments of the present disclosure are not limited thereto.
[0415] The alkaline earth metal compound may be selected from
alkaline earth metal compounds (such as BaO, SrO, CaO,
Ba.sub.xSr.sub.1-xO (0<x<1), and/or Ba.sub.xCa.sub.1-xO
(0<x<1)). In one embodiment, the alkaline earth metal
compound may be selected from BaO, SrO, and CaO, but embodiments of
the present disclosure are not limited thereto.
[0416] The rare earth metal compound may be selected from
YbF.sub.3, ScF.sub.3, ScO.sub.3, Y.sub.2O.sub.3, Ce.sub.2O.sub.3,
GdF.sub.3, and TbF.sub.3. In one embodiment, the rare earth metal
compound may be selected from YbF.sub.3, ScF.sub.3, TbF.sub.3,
YbI.sub.3, ScI.sub.3, and TbI.sub.3, but embodiments of the present
disclosure are not limited thereto.
[0417] The alkali metal complex, the alkaline earth metal complex,
and the rare earth metal complex may include an alkali metal ion,
an alkaline earth metal ion, and a rare earth metal ion,
respectively, as described above, and each ligand coordinated with
a metal ion of the alkali metal complex, the alkaline earth metal
complex, and the rare earth metal complex may independently be
selected from hydroxyquinoline, hydroxyisoquinoline,
hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine,
hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxydiphenyl
oxadiazole, hydroxydiphenyl thiadiazole, hydroxyphenyl pyridine,
hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole,
bipyridine, phenanthroline, and cyclopentadiene, but embodiments of
the present disclosure are not limited thereto.
[0418] The electron injection layer may include (e.g., consist of)
an alkali metal, an alkaline earth metal, a rare earth metal, an
alkali metal compound, an alkaline earth metal compound, a rare
earth metal compound, an alkali metal complex, an alkaline earth
metal complex, a rare earth metal complex, or a combination
thereof, as described above. In one or more embodiments, the
electron injection layer may further include an organic material.
When the electron injection layer further includes an organic
material, the alkali metal, the alkaline earth metal, the rare
earth metal, the alkali metal compound, the alkaline earth metal
compound, the rare earth metal compound, the alkali metal complex,
the alkaline earth metal complex, the rare earth metal complex, or
the combination thereof may be homogeneously or non-homogeneously
dispersed in a matrix including the organic material.
[0419] The thickness of the electron injection layer may be about 1
.ANG. to about 100 .ANG., and in some embodiments, about 3 .ANG. to
about 90 .ANG.. When the thickness of the electron injection layer
is within these ranges, the electron injection layer may have
satisfactory electron injection characteristics without a
substantial increase in driving voltage.
[0420] At least one layer selected from the electron transport
layer and the electron injection layer may include the alkali
metal, the alkaline earth metal, the rare earth metal, the alkali
metal compound, the alkaline earth metal compound, the rare earth
metal compound, the alkali metal complex, the alkaline earth metal
complex, the rare earth metal complex, or the combination
thereof.
Second Electrode 190
[0421] The second electrode 190 may be on the organic layer 150.
The second electrode 190 may be a cathode that is an electron
injection electrode, and in this regard, the material for forming
the second electrode 190 may be a material having a low work
function, and such a material may be a metal, an alloy, an
electrically conductive compound, or a combination thereof.
[0422] The second electrode 190 may include at least one selected
from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al),
aluminum-lithium (Al--Li), calcium (Ca), magnesium-indium (Mg--In),
magnesium-silver (Mg--Ag), ITO, and IZO, but embodiments of the
present disclosure are not limited thereto. The second electrode
190 may be a transmissive electrode, a semi-transmissive electrode,
or a reflective electrode.
[0423] The second electrode 190 may have a single-layer structure,
or a multi-layer structure including two or more layers.
Description of FIGS. 2 to 5
[0424] An organic light-emitting device 20 represented by FIG. 2
includes a first capping layer 210, a first electrode 110, an
organic layer 150, and a second electrode 190 sequentially stacked
in this stated order. An organic light-emitting device 30
represented by FIG. 3 includes a first electrode 110, an organic
layer 150, a second electrode 190, and a second capping layer 220
sequentially stacked in this stated order. An organic
light-emitting device 40 represented by FIG. 4 includes a first
capping layer 210, a first electrode 110, an organic layer 150, a
second electrode 190, and a second capping layer 220.
[0425] Regarding FIGS. 2 to 4, the first electrode 110, the organic
layer 150, and the second electrode 190 may each be the same as
described herein in connection with FIG. 1.
[0426] In the organic layer 150 of each of the organic
light-emitting devices 20 and 40, light generated in an emission
layer may pass through the first electrode 110 (which may be a
semi-transmissive electrode or a transmissive electrode) and the
first capping layer 210 toward the outside. In the organic layer
150 of each of the organic light-emitting devices 30 and 40, light
generated in an emission layer may pass through the second
electrode 190 (which may be a semi-transmissive electrode or a
transmissive electrode) and the second capping layer 220 toward the
outside.
[0427] The first capping layer 210 and the second capping layer 220
may increase the external luminescent efficiency of the device
according to the principle of constructive interference.
[0428] The first capping layer 210 and the second capping layer 220
may each independently be a capping layer including an organic
material, an inorganic capping layer including an inorganic
material, or a composite capping layer including an organic
material and an inorganic material.
[0429] At least one selected from the first capping layer 210 and
the second capping layer 220 may include at least one material
selected from carbocyclic compounds, heterocyclic compounds,
amine-based compounds, porphyrin derivatives, phthalocyanine
derivatives, naphthalocyanine derivatives, alkali metal-based
complexes, and alkaline earth metal-based complexes. The
carbocyclic compound, the heterocyclic compound, and the
amine-based compound may each be optionally substituted with a
substituent containing at least one element selected from O, N, S,
Se, silicon (Si), fluorine (F), chlorine (Cl), bromine (Br), and
iodine (I).
[0430] In one embodiment, at least one selected from the first
capping layer 210 and the second capping layer 220 may include an
amine-based compound.
[0431] In one embodiment, at least one selected from the first
capping layer 210 and the second capping layer 220 may include the
compound represented by Formula 201 and/or the compound represented
by Formula 202.
[0432] In one or more embodiments, at least one selected from the
first capping layer 210 and the second capping layer 220 may
include a compound selected from Compounds HT28 to HT33 and
Compounds CP1 to CP5, but embodiments of the present disclosure are
not limited thereto.
##STR00234##
[0433] FIG. 5 is a schematic view of an organic light-emitting
device 11 according to an embodiment of the present disclosure. The
organic light-emitting device 11 may include a first electrode 110,
a hole transport layer 151, an emission auxiliary layer 153, an
emission layer 155, a buffer layer 156, an electron transport layer
157, an electron injection layer 159, and a second electrode 190
sequentially stacked in this stated order.
[0434] The layers included in the organic light-emitting device 11
of FIG. 5 may be the same as described above.
[0435] Hereinbefore, an organic light-emitting device according to
an embodiment of the present disclosure has been described in
connection with FIGS. 1 to 5. However, embodiments of the present
disclosure are not limited thereto.
[0436] The layers constituting the hole transport region, the
emission layer, and the layers constituting the electron transport
region may be formed in a specific region using one or more
suitable methods selected from vacuum deposition, spin coating,
casting, a Langmuir-Blodgett (LB) method, ink-jet printing,
laser-printing, and laser-induced thermal imaging (LITI).
[0437] When the respective layers of the hole transport region, the
emission layer, and the respective layers of the electron transport
region are each formed by deposition, the deposition may be
performed at a deposition temperature of about 100 to about
500.degree. C., at a vacuum degree of about 10.sup.-8 to about
10.sup.-3 torr, and at a deposition rate of about 0.01 to about 100
.ANG./sec, depending on the material to be deposited in each layer,
and the structure of each layer to be formed.
[0438] When the layers constituting the hole transport region, the
emission layer, and the layers constituting the electron transport
region are each formed by spin coating, the spin coating may be
performed at a coating speed of about 2,000 rpm to about 5,000 rpm
and at a heat treatment temperature of about 80.degree. C. to
200.degree. C., depending on the material to be included in each
layer, and the structure of each layer to be formed.
General Definitions of Substituents
[0439] The term "C.sub.1-C.sub.60 alkyl group", as used herein,
refers to a linear or branched aliphatic saturated hydrocarbon
monovalent group having 1 to 60 carbon atoms, and non-limiting
examples thereof may include a methyl group, an ethyl group, a
propyl group, an isobutyl group, a sec-butyl group, a ted-butyl
group, a pentyl group, an iso-amyl group, and a hexyl group. The
term "C.sub.1-C.sub.60 alkylene group", as used herein, refers to a
divalent group having substantially the same structure as the
C.sub.1-C.sub.60 alkyl group.
[0440] The term "C.sub.2-C.sub.60 alkenyl group", as used herein,
refers to a hydrocarbon group formed by substituting at least one
carbon-carbon double bond in the body (e.g., middle) or at the
terminus of the C.sub.2-C.sub.60 alkyl group, and non-limiting
examples thereof may include an ethenyl group, a propenyl group,
and a butenyl group. The term "C.sub.2-C.sub.60 alkylene group", as
used herein, refers to a divalent group having substantially the
same structure as the C.sub.2-C.sub.60 alkyl group.
[0441] The term "C.sub.2-C.sub.60 alkynyl group", as used herein,
refers to a hydrocarbon group formed by substituting at least one
carbon-carbon triple bond in the body (e.g., middle) or at the
terminus of the C.sub.2-C.sub.60 alkyl group, and non-limiting
examples thereof may include an ethynyl group and a propynyl group.
The term "C.sub.2-C.sub.60 alkylene group", as used herein, refers
to a divalent group having substantially the same structure as the
C.sub.2-C.sub.60 alkyl group.
[0442] The term "C.sub.1-C.sub.60 alkoxy group", as used herein,
refers to a monovalent group represented by --O-A.sub.101 (wherein
A.sub.101 is a C.sub.1-C.sub.60 alkyl group), and non-limiting
examples thereof may include a methoxy group, an ethoxy group, and
an isopropyloxy group.
[0443] The term "C.sub.3-C.sub.10 cycloalkyl group", as used
herein, refers to a monovalent saturated hydrocarbon monocyclic
group having 3 to 10 carbon atoms, and non-limiting examples
thereof may include a cyclopropyl group, a cyclobutyl group, a
cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The
term "C.sub.3-C.sub.10 cycloalkylene group", as used herein, refers
to a divalent group having substantially the same structure as the
C.sub.3-C.sub.10 cycloalkyl group.
[0444] The term "C.sub.10-C.sub.10 heterocycloalkyl group", as used
herein, refers to a monovalent monocyclic group having at least one
heteroatom selected from N, O, Si, P, and S as a ring-forming atom
and 1 to 10 carbon atoms, and non-limiting examples thereof may
include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl
group, and a tetrahydrothiophenyl group. The term "C.sub.1-C.sub.10
heterocycloalkylene group", as used herein, refers to a divalent
group having substantially the same structure as the
C.sub.1-C.sub.10 heterocycloalkyl group.
[0445] The term "C.sub.3-C.sub.10 cycloalkenyl group", as used
herein, refers to a monovalent monocyclic group that has 3 to 10
carbon atoms and at least one double bond in the ring thereof and
does not have aromaticity, and non-limiting examples thereof
include a cyclopentenyl group, a cyclohexenyl group, and a
cycloheptenyl group. The term "C.sub.3-C.sub.10 cycloalkenylene
group", as used herein, refers to a divalent group having
substantially the same structure as the C.sub.3-C.sub.10
cycloalkenyl group.
[0446] The term "C.sub.1-C.sub.10 heterocycloalkenyl group", as
used herein, refers to a monovalent monocyclic group that has at
least one heteroatom selected from N, O, Si, P, and S as a
ring-forming atom, 1 to 10 carbon atoms, and at least one double
bond in its ring. Non-limiting examples of the C.sub.1-C.sub.10
heterocycloalkenyl group may include a
4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group,
and a 2,3-dihydrothiophenyl group. The term "C.sub.1-C.sub.10
heterocycloalkenylene group", as used herein, refers to a divalent
group having substantially the same structure as the
C.sub.1-C.sub.10 heterocycloalkenyl group.
[0447] The term "C.sub.6-C.sub.60 aryl group", as used herein,
refers to a monovalent group having a carbocyclic aromatic system
having 6 to 60 carbon atoms, and the term "C.sub.6-C.sub.60 arylene
group", as used herein, refers to a divalent group having a
carbocyclic aromatic system having 6 to 60 carbon atoms.
Non-limiting examples of the C.sub.6-C.sub.60 aryl group may
include a phenyl group, a naphthyl group, an anthracenyl group, a
phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When
the C.sub.6-C.sub.60 aryl group and the C.sub.6-C.sub.60 arylene
group each include two or more rings, the rings may be fused (e.g.,
condensed).
[0448] The term "C.sub.1-C.sub.60 heteroaryl group", as used
herein, refers to a monovalent group having a heterocyclic aromatic
system that has at least one heteroatom selected from N, O, Si, P,
and S as a ring-forming atom, and 1 to 60 carbon atoms. The term
"C.sub.1-C.sub.60 heteroarylene group", as used herein, refers to a
divalent group having a heterocyclic aromatic system that has at
least one heteroatom selected from N, O, Si, P, and S as a
ring-forming atom, and 1 to 60 carbon atoms. Non-limiting examples
of the C.sub.1-C.sub.60 heteroaryl group may include a pyridinyl
group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group,
a triazinyl group, a quinolinyl group, and an isoquinolinyl group.
When the C.sub.1-C.sub.60 heteroaryl group and the C.sub.1-C.sub.60
heteroarylene group each include two or more rings, the rings may
be fused (e.g., condensed).
[0449] The term "C.sub.6-C.sub.60 aryloxy group", as used herein,
refers to --O-A.sub.102 (wherein A.sub.102 is a C.sub.6-C.sub.60
aryl group), and the term "C.sub.6-C.sub.60 arylthio group" as used
herein indicates --S-A.sub.103 (wherein A.sub.103 is a
C.sub.6-C.sub.60 aryl group).
[0450] The term "monovalent non-aromatic condensed polycyclic
group", as used herein, refers to a monovalent group that has two
or more rings condensed (e.g., fused), only carbon atoms (for
example, 8 to 60 carbon atoms) as a ring forming atom, and
non-aromaticity in the entire molecular structure. A non-limiting
example of a monovalent non-aromatic condensed polycyclic group may
be a fluorenyl group. The term "divalent non-aromatic condensed
polycyclic group", as used herein, refers to a divalent group
having substantially the same structure as the monovalent
non-aromatic condensed polycyclic group.
[0451] The term "monovalent non-aromatic condensed heteropolycyclic
group", as used herein, refers to a monovalent group that has two
or more rings condensed (e.g., fused), has at least one heteroatom
selected from N, O, Si, P, and S, other than carbon atoms (for
example, 1 to 60 carbon atoms), as a ring forming atom, and has
non-aromaticity in the entire molecular structure. A non-limiting
example of a monovalent non-aromatic condensed heteropolycyclic
group may be a carbazolyl group. The term "divalent non-aromatic
condensed heteropolycyclic group", as used herein, refers to a
divalent group having substantially the same structure as the
monovalent non-aromatic condensed heteropolycyclic group.
[0452] The term "C.sub.5-C.sub.60 carbocyclic group", as used
herein, refers to a monocyclic or polycyclic group having 5 to 60
carbon atoms as the only ring-forming atoms. The term
"C.sub.5-C.sub.60 carbocyclic group", as used herein refers to an
aromatic carbocyclic group or a non-aromatic carbocyclic group. The
term "C.sub.5-C.sub.60 carbocyclic group", as used herein, refers
to a ring (such as a benzene), a monovalent group (such as a phenyl
group), or a divalent group (such as a phenylene group). In one or
more embodiments, depending on the number of substituents connected
to the C.sub.5-C.sub.60 carbocyclic group, the C.sub.5-C.sub.60
carbocyclic group may be a trivalent group or a quadrivalent
group.
[0453] The term "C.sub.1-C.sub.60 heterocyclic group", as used
herein, refers to a group having substantially the same structure
as the C.sub.1-C.sub.60 carbocyclic group, except that as a
ring-forming atom, at least one heteroatom selected from N, O, Si,
P, and S is used in addition to carbon (the number of carbon atoms
may be 1 to 60).
[0454] As used herein, at least one substituent of the substituted
C.sub.5-C.sub.60carbocyclic group, substituted C.sub.1-C.sub.60
heterocyclic group, substituted C.sub.3-C.sub.10 cycloalkylene
group, substituted C.sub.1-C.sub.10 heterocycloalkylene group,
substituted C.sub.3-C.sub.10 cycloalkenylene group, substituted
C.sub.1-C.sub.10 heterocycloalkenylene group, substituted
C.sub.6-C.sub.60 arylene group, substituted C.sub.1-C.sub.60
heteroarylene group, a substituted divalent non-aromatic condensed
polycyclic group, a substituted divalent non-aromatic condensed
heteropolycyclic group, substituted C.sub.1-C.sub.60 alkyl group,
substituted C.sub.2-C.sub.60 alkenyl group, substituted
C.sub.2-C.sub.60 alkynyl group, substituted C.sub.1-C.sub.60 alkoxy
group, substituted C.sub.3-C.sub.10 cycloalkyl group, substituted
C.sub.1-C.sub.10 heterocycloalkyl group, substituted
C.sub.3-C.sub.10 cycloalkenyl group, substituted C.sub.1-C.sub.10
heterocycloalkenyl group, substituted C.sub.6-C.sub.60 aryl group,
substituted C.sub.6-C.sub.60 aryloxy group, substituted
C.sub.6-C.sub.60 arylthio group, substituted C.sub.1-C.sub.60
heteroaryl group, substituted monovalent non-aromatic condensed
polycyclic group, and substituted monovalent non-aromatic condensed
heteropolycyclic group may be selected from the group consisting
of:
[0455] deuterium (-D), --F, --Cl, --Br, --I, a hydroxyl group, a
cyano group, a nitro group, an amidino group, a hydrazino group, a
hydrazono group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60
alkenyl group, a C.sub.2-C.sub.60 alkynyl group, and a
C.sub.1-C.sub.60 alkoxy group;
[0456] a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl
group, a C.sub.2-C.sub.60 alkynyl group, and a C.sub.1-C.sub.60
alkoxy group, each substituted with at least one selected from
deuterium, --F, --Cl, --Br, --I, a hydroxyl group, a cyano group, a
nitro group, an amidino group, a hydrazino group, a hydrazono
group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60
arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, a monovalent non-aromatic
condensed heteropolycyclic group,
--Si(Q.sub.11)(Q.sub.12)(Q.sub.13), --N(Q.sub.11)(Q.sub.12),
--B(Q.sub.11)(Q.sub.12), --C(.dbd.O)(Q.sub.11),
--S(.dbd.O).sub.2(Q.sub.11), and
--P(.dbd.O)(Q.sub.11)(Q.sub.12),
[0457] a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60
arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, and a monovalent
non-aromatic condensed heteropolycyclic group;
[0458] a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10
heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a
C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl
group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60
arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent
non-aromatic condensed polycyclic group, and a monovalent
non-aromatic condensed heteropolycyclic group, each substituted
with at least one selected from deuterium, --F, --Cl, --Br, --I, a
hydroxyl group, a cyano group, a nitro group, an amidino group, a
hydrazino group, a hydrazono group, a C.sub.1-C.sub.60 alkyl group,
a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group,
a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl
group, a C.sub.1-C.sub.10 heterocycloalkyl group, a
C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10
heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a
C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group,
a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic
condensed polycyclic group, a monovalent non-aromatic condensed
heteropolycyclic group, --Si(Q.sub.21)(Q.sub.22)(Q.sub.23),
--N(Q.sub.21)(Q.sub.22), --B(Q.sub.21)(Q.sub.22),
--C(.dbd.O)(Q.sub.21), --S(.dbd.O).sub.2(Q.sub.21), and
--P(.dbd.O)(Q.sub.21)(Q.sub.22), and
[0459] --Si(Q.sub.31)(Q.sub.32)(Q.sub.33), --N(Q.sub.31)(Q.sub.32),
--B(Q.sub.31)(Q.sub.32), --C(.dbd.O)(Q.sub.31),
--S(.dbd.O).sub.2(Q.sub.31), and
--P(.dbd.O)(Q.sub.31)(Q.sub.32),
[0460] wherein Q.sub.1 to Q.sub.3, Q.sub.11 to Q.sub.13, Q.sub.21
to Q.sub.23, and Q.sub.31 to Q.sub.33 may each independently be
selected from hydrogen, deuterium, --F, --Cl, --Br, --I, a hydroxyl
group, a cyano group, a nitro group, an amidino group, a hydrazino
group, a hydrazono group, a C.sub.1-C.sub.60 alkyl group, a
C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a
C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group,
a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10
cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a
C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryl group
substituted with a C.sub.1-C.sub.60 alkyl group, a C.sub.6-C.sub.60
aryl group substituted with a C.sub.6-C.sub.60 aryl group, a
terphenyl group, a C.sub.1-C.sub.60 heteroaryl group, a
C.sub.1-C.sub.60 heteroaryl group substituted with C.sub.1-C.sub.60
alkyl group, a C.sub.1-C.sub.60 heteroaryl group substituted with a
C.sub.6-C.sub.60 aryl group, a monovalent non-aromatic condensed
polycyclic group, and a monovalent non-aromatic condensed
heteropolycyclic group.
[0461] The term "Ph", as used herein, may refer to a phenyl group;
the term "Me", as used herein, may refer to a methyl group; the
term "Et", as used herein, may refer to an ethyl group; the terms
"ter-Bu" or "Bu.sup.t", as used herein, may refer to a ted-butyl
group; and the term "OMe," as used herein, may refer to a methoxy
group.
[0462] The term "biphenyl group", as used herein, may refer to "a
phenyl group substituted with a phenyl group". In other words, a
biphenyl group is a substituted phenyl group having a
C.sub.6-C.sub.60 aryl group as a substituent.
[0463] The term "terphenyl group", as used herein, may refer to "a
phenyl group substituted with a biphenyl group". In other words, a
terphenyl group is a substituted phenyl group having a
C.sub.6-C.sub.60 aryl group substituted with a C.sub.6-C.sub.60
aryl group.
[0464] The symbols * and *' used herein, unless defined otherwise,
may refer to a binding site to a neighboring atom in a
corresponding formula.
[0465] Hereinafter, compounds according to embodiments of the
present disclosure and an organic light-emitting device according
to embodiments of the present disclosure will be described in more
detail with reference to Synthesis Examples and Examples. The
wording "B was used instead of A" used in describing Synthesis
Examples refers to that a molar equivalent of B was used in place
of A.
EXAMPLE
Example 1-1
Manufacture of Red Organic Light-Emitting Device
[0466] An ITO glass substrate (a product of Corning Co., Ltd) with
an ITO layer having a thickness of 15 .OMEGA./cm.sup.2 (1,200
.ANG.) thereon was cut to a size of 50 mm.times.50 mm.times.0.5mm,
sonicated using isopropyl alcohol and pure water for 15 minutes,
and cleaned by exposure to ultraviolet rays and ozone for 30
minutes, and the ITO glass substrate (anode) was mounted on a
vacuum deposition apparatus.
[0467] m-MTDATA was vacuum-deposited on the ITO glass substrate to
form a hole transport layer having a thickness of 700 .ANG.. TCTA
was vacuum-deposited on the hole transport layer to form an
emission auxiliary layer having a thickness of 100 .ANG..
[0468] Compound 1-3 (host) and PD11 (dopant) were co-deposited on
the emission auxiliary layer at a weight ratio of 98:2 to form an
emission layer having a thickness of 300 .ANG..
[0469] Compound 2-9 was deposited on the emission layer to form a
buffer layer having a thickness of 100 .ANG., and Alq.sub.3 was
vacuum-deposited on the buffer layer to form an electron transport
layer having a thickness of 200 .ANG.. LiF was deposited on the
electron transport layer to form an electron injection layer having
a thickness of 10 .ANG..
[0470] Then, Al was deposited on the electron injection layer to
form a cathode having a thickness of 2,000 .ANG., thereby
completing the manufacture of an organic light-emitting device.
Examples 1-2 to 1-10 and Comparative Examples 1-1 to 1-3
[0471] Additional organic light-emitting devices were manufactured
in substantially the same manner as in Example 1-1, except that
each emission layer and each buffer layer were formed using the
compounds shown in Table 5.
Example 2-1
Manufacture of Green Organic Light-Emitting Device
[0472] An ITO glass substrate (a product of Corning Co., Ltd) with
an ITO layer having a thickness of 15 .OMEGA./cm.sup.2 (1,200
.ANG.) thereon was cut to a size of 50 mm.times.50 mm.times.0.5mm,
sonicated using isopropyl alcohol and pure water for 15 minutes
each, and cleaned by exposure to ultraviolet rays and ozone for 30
minutes, and the ITO glass substrate (anode) was mounted on a
vacuum deposition apparatus.
[0473] m-MTDATA was vacuum-deposited on the ITO glass substrate to
form a hole transport layer having a thickness of 700 .ANG.. TCTA
was vacuum-deposited on the hole transport layer to form an
emission auxiliary layer having a thickness of 100 .ANG..
[0474] Compound 1-3 (host) and PD13 (dopant) were co-deposited at a
weight ratio of 90:10 on the emission auxiliary layer to form an
emission layer having a thickness of 300 .ANG..
[0475] Compound 2-9 was deposited on the emission layer to form a
buffer layer having a thickness of 100 .ANG., and Alq.sub.3 was
vacuum-deposited on the buffer layer to form an electron transport
layer having a thickness of 200 .ANG.. LiF was deposited on the
electron transport layer to form an electron injection layer having
a thickness of 10 .ANG..
[0476] Al was deposited on the electron injection layer to form a
cathode having a thickness of 2,000 .ANG., thereby completing the
manufacture of an organic light-emitting device.
Examples 2-2 to 2-5 and Comparative Examples 2-1 to 2-3
[0477] Additional organic light-emitting devices were manufactured
in substantially the same manner as in Example 2-1, except that
each emission layer and each buffer layer were formed using the
compounds shown in Table 5.
Example 2-6
[0478] An organic light-emitting device was manufactured in
substantially the same manner as in Example 2-1, except that in
forming the emission layer, Compound 1-3 (first host), CBP (second
host), and PD13 (dopant) were co-deposited at a weight ratio of
50:50:10.
Examples 2-7 to 2-10
[0479] Additional organic light-emitting devices were manufactured
in substantially the same manner as in Example 2-6, except that
each emission layer and each buffer layer were formed using the
compounds shown in Table 6.
Examples 2-11 to 2-20
[0480] Additional organic light-emitting devices were manufactured
in substantially the same manner as in Example 2-1, except that 1
wt % F4-TCNQ was doped in forming the hole transport layer, and the
compounds shown in Table 5 were used in forming the emission layer
and the buffer layer.
Evaluation Example 1
[0481] The driving voltage and efficiency of each of the organic
light-emitting devices of Examples 1-1 to 1-5 and 2-1 to 2-20 and
Comparative Examples 1-1 to 1-3 and 2-1 to 2-3 were measured using
a Keithley SMU 236 at 5 mA/cm.sup.2. The results thereof are shown
in Tables 5 and 6:
TABLE-US-00005 TABLE 5 Emission layer Weight ratio Driving (host)
Buffer layer (host:dopant) voltage (V) Efficiency (cd/A) Example
1-1 Compound Compound 98:2 5.7 24.3 1-3 2-9 Example 1-2 Compound
Compound 98:2 5.7 24.0 1-7 2-19a Example 1-3 Compound Compound 98:2
5.5 23.7 1-7 2-149a Example 1-4 Compound Compound 98:2 5.5 23.5
1-24 2-38 Example 1-5 Compound Compound 98:2 5.6 23.9 1-24 2-58
Example 1-6 Compound Compound 98:2 5.5 24.1 1-43 2-162 Example 1-7
Compound Compound 98:2 5.4 23.8 1-71 2-176 Example 1-8 Compound
Compound 98:2 5.2 24.5 1-71 2-13 Example 1-9 Compound Compound 98:2
5.3 24.0 1-72 2-217 Example 1-10 Compound Compound 98:2 5.5 24.2
1-57 2-59a Comparative CBP Compound 98:2 5.9 22.1 Example 1-1 2-2
Comparative Compound BAlq 98:2 6.1 21.8 Example 1-2 1-3 Comparative
CBP BAlq 98:2 6.2 21.6 Example 1-3 Example 2-1 Compound Compound
90:10 5.8 39.8 1-3 2-9 Example 2-2 Compound Compound 90:10 5.7 40.3
1-30 2-48 Example 2-3 Compound Compound 90:10 5.8 40.7 1-72 2-136a
Example 2-4 Compound Compound 90:10 5.6 41.9 1-53 2-1103 Example
2-5 Compound Compound 90:10 5.7 41.3 1-56 2-162 Example 2-11
Compound Compound 90:10 5.3 41.7 1-9 2-2a Example 2-12 Compound
Compound 90:10 5.4 42.0 1-9 2-166 Example 2-13 Compound Compound
90:10 5.2 41.5 1-25 2-14a Example 2-14 Compound Compound 90:10 5.3
41.9 1-34 2-42a Example 2-15 Compound Compound 90:10 5.3 42.7 1-44
2-152a Example 2-16 Compound Compound 90:10 5.4 42.3 1-44 2-114
Example 2-17 Compound Compound 90:10 5.5 41.6 1-56 2-124 Example
2-18 Compound Compound 90:10 5.2 41.8 1-66 2-200 Example 2-19
Compound Compound 90:10 5.4 42.3 1-70 2-251 Example 2-20 Compound
Compound 90:10 5.3 42.6 1-84 2-245 Comparative CBP Compound 90:10
5.9 38.7 Example 2-1 2-9 Comparative Compound BAlq 90:10 6.0 36.8
Example 2-2 1-3 Comparative CBP BAlq 90:10 6.1 36.1 Example 2-3
TABLE-US-00006 TABLE 6 Emission layer Weight ratio (first
host:second (first host:second Driving Efficiency host) Buffer
layer host:dopant) voltage (V) (cd/A) Example 2-6 Compound1-1:CPB
Compound 50:50:10 5.8 40.8 2-9 Example 2-7 Compound 1-3:Compound
Compound 50:50:10 5.5 41.7 1-72 2-48 Example 2-8 Compound
1-76:Compound Compound 50:50:10 5.7 41.6 CBP 2-136a Example 2-9
Compound 1-24:Compound Compound 50:50:10 5.4 42.0 1-69 2-103
Example 2- Compound 1-14:Compound Compound 50:50:10 5.5 42.3 10
1-53 2-162
##STR00235## ##STR00236##
[0482] From Tables 5 and 6, it is seen that each of the organic
light-emitting devices of Examples 1-1 to 1-10 have lower driving
voltage and higher efficiency than each of the organic
light-emitting devices of Comparative Examples 1-1 to 1-3, and each
of the organic light-emitting devices of Examples 2-1 to 2-20 have
lower driving voltage and higher efficiency than each of the
organic light-emitting devices of Comparative Examples 2-1 to
2-3.
[0483] An organic light-emitting device according to an embodiment
of the present disclosure may have low driving voltage and high
efficiency.
[0484] It should be understood that the embodiments described
herein should be considered in a descriptive sense only and not for
purposes of limitation. Descriptions of features or aspects within
each embodiment should typically be considered as being available
for other similar features or aspects in other embodiments.
[0485] As used herein, the terms "use", "using", and "used" may be
considered synonymous with the terms "utilize", "utilizing", and
"utilized", respectively. Further, the use of "may" when describing
embodiments of the present disclosure refers to "one or more
embodiments of the present disclosure".
[0486] As used herein, the terms "substantially", "about", and
similar terms are used as terms of approximation and not as terms
of degree, and are intended to account for the inherent deviations
in measured or calculated values that would be recognized by those
of ordinary skill in the art.
[0487] Also, any numerical range recited herein is intended to
include all sub-ranges of the same numerical precision subsumed
within the recited range. For example, a range of "1.0 to 10.0" is
intended to include all subranges between (and including) the
recited minimum value of 1.0 and the recited maximum value of 10.0,
that is, having a minimum value equal to or greater than 1.0 and a
maximum value equal to or less than 10.0, such as, for example, 2.4
to 7.6. Any maximum numerical limitation recited herein is intended
to include all lower numerical limitations subsumed therein and any
minimum numerical limitation recited in this specification is
intended to include all higher numerical limitations subsumed
therein. Accordingly, Applicant reserves the right to amend this
specification, including the claims, to expressly recite any
sub-range subsumed within the ranges expressly recited herein.
[0488] While one or more embodiments have been described with
reference to the drawings, it will be understood by those of
ordinary skill in the art that various changes in form and details
may be made therein without departing from the spirit and scope of
the present disclosure as defined by the following claims and
equivalents thereof.
* * * * *